


The Real Deal

by SBlackmane



Category: Original Work
Genre: All the bad TV tropes you never knew you wanted, Awkward Conversations, Awkward Romance, But they're always right, Character building, Comedy, Denial of Feelings, Eventual Smut, F/M, I Wrote This Instead of Sleeping, Idiots in Love, It's totally a rom-com, Original Character(s), Romance, Sexual Tension, Terrible sidekicks, When You're Best Friends With Your Boss, You want to know what this is? It's basically every rom-com movie rolled into one, contemporary fiction, so don't forget popcorn, way too many pop culture references
Language: English
Status: In-Progress
Published: 2018-07-13
Updated: 2018-07-17
Packaged: 2019-06-09 18:47:31
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 25,694
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15273954
Author URL: https://archiveofourown.org/users/SBlackmane/pseuds/SBlackmane
Summary: Jack Bartlett was lost before meeting Anna Baker, and can't possibly live without her. It seems he's finally found the perfect woman. She's the piece of the puzzle he's been missing in his life, but there's just one tiny problem. She's not his girlfriend, she's his assistant.Anna has been perfectly content with denying her repressed feelings for her boss, and has instead blamed their closeness on how personal their work relationship has gotten. But when Jack asks that she start posing as his love interest to keep his mother happy, and his family from questioning his relationship status, things get awkward, both at work and everywhere else.With Anna's career hanging in the balance, the two must pull off the hitch without being discovered, until Jack can manage to snag a real relationship. But both may discover that this faux pas of theirs might be more genuine than either ever realized. It might actually be the kind of love that both have been missing, and can't live without.It might actually be the 'real deal'.





	1. Lost

**Author's Note:**

> So I thought I'd take a break from my fandom related works and write some original fiction for a while. Mostly character building, skimpy on the setting, but heavy on the contemporary style. And I'm so deeply sorry to anyone that contours their make-up, and anyone named Krystal (with a K). Know that your sacrifice has not been in vain.
> 
> Hope you enjoy ;)

They had been lost.

Both of them.

The cab driver was new, had never been to that address before, and neither had she. It was almost an hour drive from her flat, and if not for the salary offered, she would never even bother going to an interview for a job that far away from home. She knew it would just be a hassle with the cab and bus fare, but the hours and the pay seemed worth it. So she and Bob the Driver navigated the busy street searching for building 219.

She almost didn't make it on time, with maybe two minutes to spare. She stared at the elevator for a cool five seconds before deciding the stairs might be quicker.

So there she was, running up the steps carrying her dime store heels so they wouldn't snap, rummaging through her knock off Louis Vuitton for her chapstick, and tripping on the next step as she tried to put it on. She would have lipstick, but as was her luck lately, it broke when she tried to put it on in the cab. So she'd stuffed it back in her purse, along with the receipt she used to wipe off the smudge that was already applied.

Suffice to say, she wasn't off to a good start when she shoved open the door to the reception area, hopped in with one shoe on, then the other, saying to the lady behind the desk, "I'm so sorry I'm...late?"

The last word came out just as she was turning around, and got an eyeful of two other women-beautiful, buxom women dressed to the nine in skimpy clothes and each wearing six inch heels-also waiting to be interviewed. Her eyes glazed over the first; blonde with glossy lips, in a red dress, sporting a _real_ Louis Vuitton, judging by the flawless stitching. The second, a shapely brunette, thick, luscious curls piled high, in a classic "little black dress".

At least five, possibly ten years younger, texting on their iPhones, their perfect french manicured nails click-clacking on their screens like birds annoyingly tapping a window pane.

 _Shit_ , she thought. _There's no way this guy's going to hire me. No matter how much education or job experience I have._ Most likely he was a desperado with a sagging wife, who wanted some excitement to spur the old stud, in a manner of speaking. If he was _under_ forty, and _not_ married, likely he was just as much of a pig. Not that Anna looked terrible for thirty, could easily squeeze into a size 4, but _come on_...

There was no way she could compete with these women in looks.

"Just have a seat," said the receptionist behind the desk, an aging woman with more grey than blonde, and more crow's feet than actual crows. But she seemed friendly.

Brushing chestnut hair from her face, and adjusting her bag on her shoulder, Anna waltzed as smoothly as possible over to the seat between the Playboy Bunny and Business Barbie, then settled in. Boy, did she feel self conscious, and started to rethink ever sending in her resume, as she tapped one scuffed heel with the other under her chair. When she caught the receptionist's gaze the elderly woman smiled kindly.

Anna gave her best in return, but the acid in the back of her throat was creeping up.

* * *

Jack was lost.

Completely and irrevocably lost.

He smeared a hand across his face and pretended to be riveted by the redhead across from him that smacked her gum and told him all about Gerry that lived across from her and how he was in bed with someone that wasn't his wife. Sentence after sentence just kept coming out of her mouth and wouldn't stop, and every time he'd try to open his to politely excuse her from the interview, she'd just keep going on to another point in the story.

And her snort-laugh. God help him. His eyes glazed over and every second threatened to close until that grunt-snort of a sound would wake him up.

On and on it went for about twenty minutes until he couldn't take it anymore. That, and the constant leaning forward in her seat to show off her breasts, practically screaming in his face with the way they tumbled over her push-up bra. This was six now, six people he'd interviewed, that made him wish he wasn't losing Andy. Andy was great, and Andy could type a correctly spelled sentence. But Andy was leaving, and Jack was suffering for it now.

He never should've listened to his receptionist when she suggested he hire another woman for the workplace, but he didn't want to look sexist if he only interviewed men. Of course, he'd _definitely_ look sexist if he hired any one of the bimbos that came into his office that day with their tits hanging out unprofessionally. Finally, after what felt like hours, the redhead left, with his promise of "giving her a call", rolling his eyes after she was gone.

And _then_...

In she walked.

Anna Baker.

She was only maybe five two, five three tops, with brown hair falling out of her clip, that she constantly brushed behind her ear like it was habit. Deep brown eyes that were a bit smoky, though no lipstick, and instead he was met with two naturally rosey, and perfectly pouting lips. Nervously brushing her black pencil skirt before sitting down, then adjusting the collar of a white cotton blouse that was missing a button near her waist line.

He blinked, and realized she was real. Not only was she real, but she was _real_.

As in down to earth, and seemed like just his kind of girl. Not lacquered with inch thick makeup, nor was she popping bubble gum, and forget the hair flipping, or twirling, nah this woman wasn't making a single unwarranted pass at him. She was... _perfect_. But he wanted to slap himself as soon as that thought crossed his mind. _Keep it together, Jack, you're interviewing her, not asking her on a date. Off limits_.

But she wasn't wearing a ring, he noticed.

"Miss Baker?" he addressed, "It... _is_ Miss, right?" She nodded. _Shit, she isn't married_ , he thought, heart pounding in his chest. _Okay, focus, Jack. Focus_. "I read your resume. Looks good."

"Uh, good," she repeated, and for a few seconds it got weird.

He stared.

She stared back.

Not the kind of "love at first sight" moment when two people gazed at one another starry-eyed or anything, but the bad type of awkward staring that belonged in a quirky rom-com.

"So, I uh-"

"You know what, this was a bad idea," she interrupted, and rose from her seat, scrambling for her purse. "I-It was a mistake to come here, I mean..." She floundered for a moment. "I mean you are a _really_ attractive guy, and there are _really_ beautiful women out there waiting to be interviewed by you, and you're probably one of those guys that hires a woman based on their looks so he's got something hot to look at every day, and I just-"

She turned and immediately left.

"Wait, wait, _hold on_ ," he said, and she paused in the doorway. "You honestly think I'm one of _those_ guys?" he asked, and she made a half turn to glance back at him, stabbing him with a _look_. He wanted to laugh. "You don't even know me. You've literally been in my office for like... five seconds."

"Oh, trust me, I know your type," she told him, and he gaped at her in confusion. She cursed at herself. "I can't _believe_ I rode around for twenty minutes trying to find this place, got double charged on my cab fare and nearly broke my ankle trying to run up those stairs so I wouldn't be late to this interview!" she exclaimed. "Of all the stupid things!"

"You know there's an elevator... right?" he asked, and she glowered, hair falling in her face once more that she blew away but it fell right back.

"I thought the stairs would be quicker."

Jack was still stuck on the 'I know your type' thing. "Wait, my _type_? What do you mean my _type_?" he asked, starting to get flustered, rising from his seat to stand with his arms folded, daring her to answer logically. She looked him up and down, from top to bottom, taking in everything from his parted black hair, to his suit, to the Rolex on his wrist. "Look, lady, I think you've got the wrong idea-"

"Oh, no, I think I've pegged you perfectly, actually," she corrected.

"Oh really?" he challenged, unable to resist, and quite frankly he was intrigued by this woman's guile.

"Yeah, really," she said. "You hotshot lawyers are all the same. And you, what, drive a Porsche or something too, I'm guessing? So you probably thought that since you can't go out and dive into the dating pool anymore because you've already scratched out too many numbers in your little black book, you figured, 'What better woman than one who brings me coffee and picks up my dry cleaning?'-"

"Whoa, this is not-"

"-And of course you're a lawyer, so you figure you've got you're sexual harassment case in the bag, am I right?"

"Wait, what?!" he exclaimed, but she was already tearing out the door in a huff and marching across the reception area, making the women waiting to be interviewed eye her questioningly. And meanwhile, Jack was floored. Wondering at what point in the conversation with a woman he _just met_ should it turn into a sexual harassment seminar, and how in the _hell_ he could be verbally blasted so fast like that.

He was _really_ lost in translation here.

"Am I dreaming, or did I actually show up for work today?" he asked himself.

He stood in the doorway of his office for another minute or so, still reeling from the way she just so viscously tore him down for being a chauvinistic pig, before he realized she was getting away, and bolted for the exit. Evelyn watched from behind her desk with a quizzical expression as he tore through the waiting room, almost knocking over the innocent by-standing fern in attempt to catch her before she left the building.

She had entirely the wrong idea about him, and while he was pretty insulted, this woman was a firecracker with a college degree, that could type more than forty words per minute, and he damned sure wasn't going to let her slip through his fingers.

He knew in that moment that he absolutely, undeniably, _one hundred percent_ needed this woman in his life.

So maybe it wasn't love at first sight, so much as it was love at first verbal assault.

He ran to the elevator, but it was already closed, so he rushed to the stairwell. He just barely managed to catch her on the bottom floor before she escaped through the revolving door and shouted, "Can you start tomorrow?!"

She skidded to a halt, then whipped around. "What?!" she called up to him, and he bounded down the last flight of steps after her.

"Can you start... tomorrow?" he asked, breathlessly, when he reached the bottom, sliding a little on the freshly waxed checkerboard tile. "Look, I'm not what you think I am, I _don't_ hire women based on their looks, and in fact, I don't just hire women. My last assistant, Andy-"

"As in Andrea?"

"As in _Andrew_ ," he huffed, "Was a college student taking night classes, and put in his notice last week after he graduated. Otherwise I wouldn't even be looking for someone new. And you," She folded her arms and tilted her chin, "You have a degree, which tells me that unlike the last woman I spoke to, you have something else to talk about than 'how many women Gerry can sleep with behind his wife's back in one week'."

She snorted at that, covering her mouth. "How many?"

"So I-wait what?"

"How many women?" she asked. "Can Gerry sleep with in one week?"

He let out a sigh, relaxing his shoulders. Well, she wasn't running away yet. "Eight, apparently."

"Wow, eight," she said, raising a brow. Then she sighed. "Look, I uh... when I saw those women in your office I assumed, I mean... two young, gorgeous women-"

"There were _three_ , but one ran out, and I had to chase her down," he said, and she eyed him incredulously. "Sorry, I-that's not appropriate, I know, but-well-" He ran his hand through his hair and sighed. "Evelyn was the one who scheduled the interviews. It's entirely a coincidence, I assure you. I'm-I'm really not that kind of guy. And no, I don't drive a Porsche. I have an Audi." She eyed him curiously, and he shrugged. "It's practical."

"Hmph." She glanced down. "Nice watch."

He checked his time piece. "Thanks. Christmas gift. From somebody with better taste than me."

She laughed. "Oh, wait, I get it. You're not a shallow tool bag, you're just a _cheapskate_."

He smirked a little. "With watches, yes. Women? That's... well, that's probably a subject best avoided," he winced. She regarded him for a moment still.

"So it was your receptionist that scheduled hot women back to back, huh?" she asked, and he nodded.

"I think she thinks that because I'm not married, nor am I seeing anyone, that it gives her a free pass to throw women my way," he said, then leaned closer, muttering, "I think she's conspiring with my mom."

Again, Anna chuckled a little, and he smiled. "Alright, fine. Tomorrow. Should I be here early? Or..."

"When the office opens," he told her with a nod. "You know, usually it's the potential employee that has to convince someone why they should be hired... not the other way around."

She shrugged, saying, "Eh, well, you made a pretty good case for yourself. Is this how you win _all_ your cases? Chase the judges down and practically beg for it?"

He rolled his eyes, smiling, and said, "No, but it can't hurt to have a good closing argument."

"True," she said, eyes passing over him once more.

"Oh, right, one more thing," he said. "Uhm, might need to go shopping though. Your outfit is, uh-"

"Dammit I _knew_ it!" she scathed, pointing an accusing finger, and it was pretty adorable, if he were being honest. "You expect me to wear tight, showy little dresses so you can-"

"Oh, god no! Your uh..." He gestered to her top. "Your blouse is missing a button."

She looked down, saw the absence of a button and paled, pinching her brow in embarrassment. Meanwhile, Jack was already fishing for his wallet. "It's an old shirt, and I didn't-It was all I had and I didn't realize-"

"Here," he said, holding out his credit card. "Just buy whatever you need and bring me the receipt."

"Oh, no I-I can't-"

"I can just take it out of your pay, if it's that big of a deal. So... just keep it under a thousand. That's my card limit."

"A thousand dollars?!" she squeeked, then glanced around as if someone might be watching them, facing turning pink. "Have you lost your damned mind?"

"As good as I'm going to pay you, trust me, you can afford it... Who's the cheapskate now?" he quipped.

"Oh, don't give me that, I'm not just gonna-" She scowled. "This is ridiculous!"

 _What's ridiculous is that every other woman I met would jump at the chance to clean out my wallet_ , he thought. But all loss of sense aside, he could see she needed this job, and frankly, he needed _her_. He couldn't explain the feeling that came over him, but he had this thought that if he didn't hire this woman he would regret it. "Uh, okay, five hundred? I mean, I don't really know anything about women's fashion, so... you've got me in a box here."

"Try a hundred."

"A hundred bucks? Seriously? What could you possibly buy for a hundred bucks?"

" _A lot_ ," she said. "And it's _all_ I'll spend."

"No, just... just take the five hundred."

She huffed, folding her arms. "Two hundred."

"Five."

"Two-fifty."

It was a standoff between them for a moment. There was no winning with this woman. He briefly wondered to himself _how_ he was able to win as many cases as he had. But usually women salivated at the sight of his credit card, and this one was looking at it like it would bite her. He sighed. "What is this, a hostage negotiation?... Don't women normally spend that much money on just their shoes?" he asked.

She glanced down at her feet, then so did he.

He kneaded his brow. "Okay, whatever, spend however much-or _little_ -you want."

She quirked a brow. "Now, was that so hard?" she asked him with a smirk. Then she held out her hand. He placed the card in it, feeling dazed, then heard, "Thank you for the hostage... You need anything while I'm out?"

"No, wait yeah, uh lunch if you want. You like burgers?"

"Yeah. The place down the street?" He nodded. Before he knew what was happening, she took his order, they argued over regular or diet Coke, Anna trying to convince him the ingredients in diet _anything_ were more unhealthy than the regular. They spent another twenty minutes talking, before both realized they had places to be and things to do. She absently straightened his lopsided tie, then finally left, and Jack's heart sped up.

It all just felt so natural. Like she'd all but kissed him on the cheek and said, 'Have a great day at work, honey.' Like they'd known one another for years. It felt so surreal.

And just like that, Anna was in his life. It was like a missing piece of a puzzle suddenly found.

They just clicked. Just like that.

And that was it. That was how two lost people finally found eachother.

Two people that would probably be miserable and lonely otherwise. But there was just one problem with the arrangement.

He'd _hired_ her, when he should've asked her out instead.

* * *

_One Year Later_

"Anna, are you going to get that?" Tim asked with a groan, half groggy, and irritated at her phone buzzing with a text after 10 pm.

"Dammit," she mumbled, rolling over and fumbling for her cellphone in the dark. She knocked it off her cheap press board nightstand in the process, and slid out of bed to retrieve it from the carpet, on her hands and knees, feeling around in the dark before she found it, lighting up the screen. The notification blazed across. She rolled her eyes. A text from Jack, saying, 'HELP ME.'

'What's wrong?' she typed in reply, rubbing her eyes, then checking to make sure she typed it correctly, still half asleep at the moment.

Her phone buzzed in her hand with, 'She likes Snapchat... And I mean she REALLY likes Snapchat.'

She scoffed. 'That's what you get for letting Mark set you up with people. Haven't you learned your lesson already?'

'It was a moment of weakness. Trust me, it definitely won't happen again. Can you call me so I can get out of here?'

'Please?' he added, a second later.

Rolling her eyes and shaking her head, she pried herself from the floor to make her way down the hall and into the living room, flipping on the light. She passed the mirror and noticed that her t-shirt was on backwards, but ignored it. Behind her, Tim was grumbling about being bothered so late, making her sigh. Clearing her throat so that she didn't sound like a dying cat, she dialed Jack's cell and tapped her foot as it rang.

* * *

Miles away, Jack winced at the loud speakers blasting what passed for dance music in a nightclub, while across from him a blonde twenty-something was shouting over the noise and he pretended to listen while he was texting Anna under the table. He had no idea what he would do without Anna sometimes. She was always there when he needed her, and even sometimes when he didn't.

More than just cowarkers, they'd become friends in the months of knowing her. He still kicked himself mentally for never asking her out, but it was for the best. She needed the paycheck, and she was really good at her job. She was always on time, never missed a day, never missed a meeting, and she got along great with Evelyn. Mark too, but he was a pig. _Actually_ a pig, like she assumed Jack to be when they met.

Great lawyer, great friend, but terrible when it came to women. And in an attempt to get over the mile long streak of celibacy, Jack foolishly allowed Mark to set him up with a date. He happily answered the phone when Anna called so that he could tell Kristy?-wait, no, _Krystal_ -that it was important, and that he had to take it, shooting her an apologetic glance. "Hey, Bill, yeah, hold on one moment."

"Jack? What is all that noise?" Anna asked as he was rushing out the door of the club so that he could hear. "Is...is that _dubstep_?"

"Don't ask," he told her as he walked by the bouncer, nodding his head, then holding the rope open for him. He jogged across the street. He let out a sigh when he was finally free of the ear splitting sounds. "Thank you," he then told her.

"That bad, huh?"

"Yeah. Spent fifteen minutes watching her take selfies. Just shoot me at this point."

"I should. What the hell are you doing at a club?... Clubbing, Jack? Really?"

He sighed. "I'm _thirty_ -five, Anna, not _sixty_ -five. I still have a pulse." He glanced back at the door, then muttered, "Okay, I won't lie, I think my blood pressure is probably way too high right now, but in my defense, that's more to do with the date, not the establishment."

She huffed. "Yeah, uh-huh, sure it is... You know, Jack, this isn't The Devil Wears Prada," she told him. "I'm not Anne Hathaway, and you are _not_ Meryl Streep."

"Oh, I don't know. I think I'd look pretty good holding a Chanel handbag," he joked, and she laughed. He loved making her laugh. It was the best sound to hear, like the clouds were parting. Even better was seeing her smile. Seconds later her boyfriend was yelling in the background. Man he really hated that Tim character. Something about him just made Jack's teeth grind consistantly. "Tim staying over again?" he asked.

"Yeah, he uh...I'll be back in a minute babe!" She moved away from the the mouth piece to yell. "Yeah, he stayed over," she concluded. "So...Christina's a flop, huh?"

"Krystal, actually... with a K."

"Oh, yeah, that's worse... Well, at least she's not Jenna."

He groaned. "Oh no, don't remind me," he begged. "I don't want flashbacks of that."

"What, you don't like _contouring_ , Jack?" Anna giggled.

Ugh. What a date that was. Under the limelight, Jenna looked gorgeous, but once she stepped under a flourescent lamp she looked like Bozo the Clown, and like an idiot, he reacted, laughing, seriously offending Jenna. And, of course, like an even bigger idiot, he put his foot in his mouth when he chose to commentate. He ended up with a fifty dollar martini splashed in his face, and stuck with the check.

"Oh sure," he said, dripping with sarcasm. "Boy do I love my dates looking like a paint-by-number." Anna laughed again. "Well, again thanks. I guess I should let you get some sleep. I'll see you Monday?"

"You got it, Champ," she said, then hung up the phone.

Jack stared for a minute at her contact photo, taken from her social media account, and sighed. "Why can't I just have someone like her?" he asked himself.

* * *

Back at her flat, after hanging up the call, Anna sighed, tapping her phone against her forehead a couple of times, cursing herself. She was wide awake now, and slowly she made her way back to her room to see Tim was already passed out, dead to the world, it seemed. She flipped on the TV and turned the volume down, only for Tim to grumble in his sleep about the "damn TV", so she turned it off.

She lay back against her pillow and stared at the ceiling instead.

As much as Jack drove her crazy sometimes, forgetting to pick up his suit from the dry cleaners before a meeting, or calling her in the middle of the night to bail him out of a bad date, sometimes just calling to ask her opinion about something... 'Should I wear the white shirt, or the black with the black suit? Is that still a thing?' or 'What year did Barry Manilow die? Or wait, is he still alive?'...

As nuts as he drove her, still, life would be boring without him in it, and she knew that. She was grateful every day that she ever walked into his office looking for a job, and thankful she didn't walk away when he offered her one. She'd been wrong about him that day. Sure, he had his quirks, his pet peeves, but he really wasn't what she thought he was. He wasn't a chauvinist, he didn't objectify women, and was actually a pretty decent guy.

Sometimes it just didn't seem fair that women like Krystal got to go out with him, and here she was, stuck with Tim. Not that Tim was terrible, but he just... wasn't Jack.

Jack Bartlett would be lost without her holding him together.

And Anna?... Anna was just plain lost.


	2. Close Calls

"You're too close to him," Linda remarked across from Anna in the bar, as she sipped her happy hour cocktail. "I mean, you're on a first name basis with your boss. That should tell you everything you need to know, sweetie."

"Lots of people are on first name basis with their boss, Lin."

"Not when they work for one of the most successful law firms in the city."

Anna slumped her shoulders and stared dismally at her lifelong friend of forty, watching as she set down her cocktail and checked her makeup with her compact, brushing honey blonde hair back into place, making that doe eyed face to make sure her mascara wasn't running. Anna sighed. She'd been feeling conflicted lately in regards to Jack, needed the advice of a friend, and that was the conclusion Linda came to. And she was right.

Too many random phone calls, too many midnight rendezvous for coffee when neither could sleep. Too many lunches that were definitely not dates, but felt suspiciously like them. Too much personal information. And too much time spent with the name _Jack_ falling from her lips. She talked about Jack more than her boyfriend. That said something about her. But it wasn't like she was in love with him, just friends. Just too close to him, that was all.

So close she might as well share his last name.

"You know what, when you're right, you're right," Anna said, picking at her salad. "I mean, I've seen the guy's underwear; how much closer could we get without living together?"

"Eww, you've seen his underwear?" Linda asked, wrinkling her nose. Anna rolled her eyes.

"I've done his laundry, of course I've seen his underwear."

"You do his laundry?!"

"I did it once, as a favor," Anna explained. "He... well, he did pay my parking ticket. And... well, I did help him file his tax return... I... Yeah, okay, out loud that just sounds..."

"Huh. So, is he a boxers or a briefs kinds of guy?"

"Well, actually, he... you know what, we're getting off topic here. This is not about his underwear, Lin." Linda shrugged, then snapped closed her compact and tucked it away. "I mean, it is, but... I don't know, what should I do? I can't quit. I need the money, and he can't even tie his shoes without me. I don't want to make things worse by telling him I'm not comfortable. He'll get the idea that I've got feelings for him or something."

"Do you?" Linda asked, before sucking on her straw. Anna snorted. She looked like a fish just then. A fish with red rouged lips. Anna stared for a moment as she processed the question and formulated an answer. _Did_ she have feelings for him?... There were some days she looked forward to going to the office on Monday morning just to be able to tell Jack about her weekend. Some moments when she found herself wishing Tim was more like Jack.

Days when they split a sub sandwich because they were both cheap, and ordered the same thing, or the day they both wholeheartly agreed that Elvis faked his death.

Some days when she'd picture what it would be like to be with a guy like him, but then other days when she'd get so frustrated by something he said, or did. But when he laughed, when he smiled... And she was certainly attracted to him, of that there had never been a doubt. Tall, dark hair, chiseled features, terrific body... "You took too long to answer, honey," said Linda, snapping her out of her musings. "You're in love with him."

"What?! No! No, I'm not-"

"Yeah, I think you are," Linda corrected. "No woman that isn't in love with her boss would ever get that dreamy eyed look when she thought about him."

Anna scowled. "I was not..." She glanced down and poked angrily at her salad, fork scraping the plate. "I was not... _dreamy eyed_ ," she contested, heat rushing to her cheeks. "I mean, yes, the man is _gorgeous_ , but... But that does not mean-"

Linda broke out in a laugh, startling the people at the next booth over. She slapped the table. "Bullshit, honey, you're in love." She grinned as she plucked the cherry from her glass and snatched it off the stem with her teeth. "But the real question is-" She paused to chew. "Does he feel the same way about you?" She quirked a shapely brow, then tossed the cherry stem in her empty glass before dabbing her lips with a napkin. "Fifty bucks says _yes_."

Anna set down her fork, giving up on the wilting salad, ready to let it die on her plate.

"He does _not_ have feelings for me, okay? I'm more like the guy's surrogate mom, if anything. Only he _has_ a mom, of whom he has a really good relationship with. I just bring him lunch, pick up his laundry, keep his life from falling apart, that stuff. I'm _not_ the love interest of that man's story. I'm telling you, I'm _not_. There is no office romance, nor will there ever be any engagement parties, or wedding bells, in our future."

"Ah, you said _our_ , not _his_ ," Linda told her, and she rolled her eyes. "You're already thinking in relationship terms. Fine, you don't believe me? Dump Tim, give him your notice, and watch what happens. I guarantee you the first thing he does is ask you out to dinner once you're available for purchase." She pursed her lips. "So do it. Quit your miserable job, and ask the man out already. Problem solved."

"I'm not in love with him," Anna argued, but to no avail. Linda still didn't believe her, and honestly, she was starting to rethink this whole asking for advice thing.

* * *

Several blocks away, Jack was also conflicted, though instead of torturing and killing a defenseless salad that never wronged him personally, he was at the bottom of a very tall drink, sitting next to Mark on a barstool, hunched over in his seat. Amid the desperate search for the bottom of the glass, he heard Mark say, "Sorry about Krystal. I really thought that one would work out. I mean, her sister said she was mature for her age."

"Yeah, real mature. What is she, twelve?! Krystal With A K spent more time taking pictures of herself 'at the club' than actually enjoying the club. Snapchatting _other men_ while on a date with _me_. If you can _call_ that a date."

He stabbed Mark with a glare as he spoke, blaming his shortsighted friend for the whole evening. But truth be told, Jack was the fool for ever letting Mark pull a number out of his phone and setting him up. Mark shrugged at the look he received, too engrossed in his own cup to really be offended by anything at the moment. "Right, because you weren't sitting there with your head down, texting Anna under the table the whole time," Mark guessed.

"No, as a matter of fact I didn't text Anna until _after_ the storm hit."

"But you _did_ text her. She bailed you out again, huh?"

"Yeah. Made up some last minute case work that popped up, told her I had to stop by the office. She believed it. A minute longer and I would've been chewing my own arm off to get away from her..." He smeared a hand across his face, then sighed, gazing longingly at the bottom of his empty glass. "I don't get why I can't just find a woman like Anna," he admitted. "I mean, she's perfect. And she gets me."

Mark pointedly set down his cup and leaned on the backrest of the barstool. "I don't get why you don't just go after _Anna_. You just said so yourself just now, she's perfect, and she gets you. Jack, the woman's a ten. Hot, and you know she can handle your train wreck of an existence that you happen to call your _life_."

"It's not even like that between us. And besides, she's already got a boyfriend. _Tim_." He scowled just saying the guy's name, and Mark chuckled.

"Man, you really don't like this guy, do you?"

"No. Something about him just doesn't feel right. I'm thinking of doing a background check. I know a guy."

"Somebody's jealous," Mark teased, and Jack rolled his eyes.

He shook his head. "No. No, I'm not jealous," he swore, but Mark didn't believe him. "I just think he's bad news. I just don't want her to get hurt. Look, this is not one of those cheesy chick flicks where the hot, savvy assistant sleeps with her boss and realizes she's in love with him, dumps her douchebag boyfriend and they live happily ever after. This is real life, Mark."

"Yeah, well, in real life, men sleep with their hot assistant all the time."

Jack huffed. "She's happily taken, Mark."

"If she was _that_ happy, she wouldn't call you up every time your date's a disaster, nor would she be meeting up with you for coffee in the middle of the night."

"We're both insomniacs," Jack explained. Mark shrugged again.

"You're just making excuses," he said. "Come on, man, _when_ are you going to wake up and realize there's something between you two? And actually _do_ something about it? Alleviate this 'unspoken sexual tension in the workplace'? And don't tell me there's not tension, because man, you are as tense as a morning after with a one night stand."

Jack was about to reply, when his phone buzzed in his pocket. When he saw the name Ron Malenack pop up, he answered, saying, "Ronnie, how's it going?" Prying himself from the barstool to step outside.

* * *

"Speak of the devil," she muttered when her phone rang, making Linda chuckle. She slid out of her seat as she answered with, "What's up?" Walking down the isle toward the entrance.

"Uh, nothing much really, I just... well, uh..."

"Everything okay, Champ?" she asked, inwardly cursing at her slip of informality, but noticing how flustered Jack sounded on the phone. She pushed open the glass door and stepped outside to a busy street, so she started around the side of the building to get away from the noise. "What's going on?"

"I need a favor," he said, with a sigh. _When do you not?_ she thought. "You remember a few months ago when I lied to my mom about being in a relationship?"

"Yeah?"

"Well, one of my dad's golfing buddies flew in yesterday, and wants to catch up. He invited me to a thing, some sort of charity ball upstate and... well, I was wondering... Can you pose as my girlfriend?"

She nearly dropped her phone on the sidewalk, but it bounced off her purse, and she dove to catch it, fumbling with it. "What?!" she exclaimed, when the phone was back to her ear. She huffed breathlessly for a moment in disbelief, then brushed her hair away from her face. "You mean to tell me you're _still_ lying to your family? What the hell's the matter with you?!" she snapped. Then she sighed. "Sorry-I-Look, Jack, just tell them the truth-"

"I can't," he said. "I already told Ronnie I was bringing a date."

"Okay? Well, then find somebody to take with you, like an _actual_ date."

"Uhm, well, here's the thing... I uh... I might've mentioned you already-"

"What?!"

"He asked me specifics about my date, and I had to come up with something, and, well, you were the first person I thought of."

She growled. "You're unbelievable," she told him. "You don't think people will notice if you're pretend dating your assistant?"

"He's flying right back out tomorrow. He'll never know. So will you? Please?... Come on, Ann, it's just for a few hours. You know more about me than I do, so it's not like it would be that hard to convince people we're dating. We just hold hands, maybe dance, and bam, it's in the bag... Whaddya say?"

"Unbelievable," she repeated, scathingly. "Alright, fine."

"Great, I'll pick you up at-"

"Wait, shit! I can't! I don't have anything to wear!"

"You've got my credit card."

She sighed, kneading her brow. "Alright, what time should I be ready?"

* * *

This was going to be a disaster. She just knew it.

But nevertheless, she stopped by a boutique that was still open, asked them if they did rentals, then picked out something reasonable, pocketing the ticket for safekeeping. Perhaps a bit conservative, considering that Jack's parents tended to run in pretty high class social circles, and the event was a ball, which meant evening gowns were expected to be worn. But there was no way she was going upstate looking like a tramp.

Jack Bartlett did have standards, after all.

So a high front, semi-low backed, full length dress in beige was the happy middle ground, and hair that was normally tossed into a plastic clip was worn down around her shoulders and ran away at the ends. Jack picked her up at the boutique, already suited, but his tie was crooked, per usual. She made a beeline for the tie as soon as they were out of the car and the valet was tossed the keys.

"What am I, ten?" he chuckled as she fixed it. "You look great, by the way."

"I'm going to pretend I didn't hear that," she told him. He rolled his eyes.

"So I can't even compliment you?"

"You're still in time out, remember?" she said, fixed his collar, then took his arm when offered. "And you owe me big time for this," she added as they ascended the steps leading into the posh estate chosen to host the event. Invitations exchanged hands, the door was opened for them both, and into the revelry they went, Jack picking up the first champagne glasses he saw on a tray and handing one to Anna.

"Trust me, I owe you everything," he muttered.

* * *

Ronnie absolutely _loved_ her, Jack noticed.

He always made this face at people when he was pretending to enjoy someone's company, but no such face was made at Anna. His interest in their shared conversation was genuine. And Anna was funny, charming, knew all the right things to say; absolutely a hit. They knew plenty about each other that as long as she didn't mention his dating mishaps, and he didn't mention Tim, they totally pulled it off.

"So, what do you do for a living?" Ronnie asked her, and she only took two seconds to respond instead of one, which wasn't bad. But Jack froze in nervousness for a moment. They didn't come up with anything in regards to her fake employment. Too last minute, not enough cue cards.

But she answered honestly. "I'm an assistant," she said.

"Oh, so you're a secretary?"

She chuckled. "No, that would be more like a receptionist," she told him. "I'm an office assistant." She glanced up at Jack. "At an accounting firm."

"Oh wow," he said. "You better watch out, Jack, her boss might steal her away from you," he teased, elbowing Jack's arm, and he feigned a smile.

"Yeah, Ann, she's, uh, she's pretty great at what she does," he said, casually slipping an arm around her waist. "If I didn't want to date her so badly I would've snagged her up as _my_ assistant." She gave a quiet noncommittal snort at that. He glanced down at her. "But I knew as soon as we met I didn't want her just bringing me coffee every morning. There was no way I was letting this one get away."

She chuckled, patting his arm, and he smiled, but his heart was racing in his chest.

"Well, I'll let you kids enjoy yourselves," Ronnie concluded, headed to the bar for another drink, and Jack glanced down to see Anna eyeing the dance floor. A slow song had started. He held out his hand for hers and she accepted, letting him lead her out onto the floor, and pull her in close, like a couple that actually enjoyed being in each other's company. She would probably lord this over him for days to come, but it was worth it at the moment.

This was probably his one and only chance at being close to her without completely ruining their friendship, or work relationship. "So, uh, what did you tell Tim?" he asked, striking up conversation. She shrugged.

"Oh, he's out of town tonight, so I just sent him a text, telling him I was going to a party."

He looked around. "Some party, huh?" She nodded. "Ann, I gotta tell you, there's something up with that guy," he confided.

She rolled her eyes and lolled her head.

"No, I'm serious. Something just feels... _off_ about him. I don't think he's right for you. I mean, he never stays at your place more than one night at a time. He never invites you to stay over at his place. And a 'consultant'? Ann, that's what most men tell women they do for a living when they don't want to admit they're unemployed."

"Okay, slow down there, cowboy," she said. "One, he's remodeling his apartment, and two, just because it's a popular scapegoat, that does not mean consulting isn't a real thing."

"Yeah, but it's too much of a coincidence."

"Jack, you are the _last_ person that should give anybody dating advice," she told him.

"You give me dating advice all the time," he countered.

"Well, that's because you _need_ it," she pointed out. "I mean, look at you. Lying about being in a relationship?" she whispered. "You know, instead of lying, you could tell the truth, and maybe free yourself up for a _real_ relationship."

"It's not like I haven't been trying," he said. "But..." He sighed. "I don't know, it's like every woman I meet is another Jenna, or a Krystal With A K." He shrugged. "The second they find out what I do for a living, and how much money I make, they're like vultures. And I don't want to look bad, so of course I offer to pay the check, and then let them floor me with a five hundred dollar drink order. Just lemme clone you, and I think I might be getting somewhere."

She burst out laughing. She didn't think he was being serious. And he probably shouldn't tell her he was. That the perfect woman for him was right there, dancing with him. "You know you wouldn't have this problem if you didn't judge a person on the first date, Jack," she told him. "Let's be real here. How many women have you actually gone on a second date with?" He opened his mouth, but then closed it. "See? You can't even remember."

"I know everything I need to know about a person in the first five minutes," he argued. "After that, it's just par for the course." He gave her an example. "When I first met Mark back in college a co-ed was throwing him out of her dorm. There he was, holding his own pants, screaming, 'Please Cecelia, she meant nothing to me, I swear!'. Then he proceeded to effectively argue that he was just a 'victim of circumstance', and she _took him back_."

She chuckled. "You're right, that's Mark in a nutshell." Jack nodded. "And yet, you still let him set you up with women."

"Only when I'm desperate," he reminded, and she rolled her eyes. "And when I met _you_..."

He trailed off as he flashed back to that moment. Stumbling into his office, hair falling out of her clip, her missing shirt button.

The way she loudly vocalized her reproval and stormed out. The way that though she mistook things on occasion, she was always so passionate about something when she felt strongly about it. She never let him get away with anything, always pushed for him to make the right choices. The way she planted her feet and stood her ground with a stance she firmly believed in. That no matter what, she always put her whole heart into something she did.

Every day. "...When you met me?" she was asking, and he blinked, realizing he hadn't said anything. That he'd been staring. And so had she, gazing expectantly up at him, biting her lip, waiting for him to elaborate. Now _this_ was one of those moments, he realized. One of those starry eyed moments like in the movies, and right then he was at a crossroads. Take the leap of faith and dive right in, tell her how he felt, or walk away before he got hurt.

The song ended, and people clapped.

He swallowed.

"I knew you were perfect for the job," he finally answered, and it was like something inside of him died as he said those words.

But she just smiled and said, "Well, of course," And patted his chest. "What would you do without me, Jack Bartlett?"

"Starve and die," he deadpanned, making her giggle.

And then Jack's miniscule window of opportunity closed completely.

* * *

_'And when I met you...'_ he had said, and she held her breath for a confession.

A confession that never came that night, and she wanted to smack herself for ever thinking it could, partly because it got her hopes up. But she settled on being able to rub it in Linda's face that she was wrong about something for a change. And she could stuff any possibility of these imagined feelings for Jack back in the closet where they belonged. There was nothing between them. They were just friends.

The night progressed unremarkably. Some more dancing, more chatting it up with Ron Malenack and his associates, trying to squeeze some free legal advice out of Jack. More pretending to be dating, the fake flirtations that maybe weren't all that fake. It was surprisingly easy to be flirty with Jack. The fact that her heart sped up and she stopped breathing whenever he slipped his arm around her waist was inconsequential.

But made it totally believable if she were convincing people she was enamoured by him.

A half a flute of champagne was not enough to floor him, so he drove them back to the city, and to her apartment complex. He opened the passanger door for her, and she was halfway out of the vehicle when she remembered, "Dammit, we've gotta go back to the boutique. I've gotta return this dress."

"Just keep it," he said, helping her out of the car while she navigated her bustling skirt.

"This is an eight hundred dollar rental, Jack," she snipped. "And if I break it, _you_ bought it."

"So?"

"We've really gotta work on how loose your wallet gets around women," she groused, and he sighed.

"I know, I know," he said, dispairingly.

"I mean, you _seriously_ need to have that checked out. This seems to be a real issue you're having."

Again, he nodded, saying, "Just... consider it a gift, for helping me to convince my dad's friend that I have a wonderful girlfriend, and that I'm not as lonely and desperate as I really am."

She shook her head at him. "When am I ever going to need an eight hundred dollar gown ever again?" she asked. He scratched his head, then shrugged.

"I'll think of something," he said, and she huffed disbelievingly at him.

She absently reached to straighten his tie, saying, "I'll pay you back, as soon as-"

He placed his hands over hers, and she froze, gaping up at him. "Don't worry about it, Ann. It's just a dress."

"It's a very expensive dress."

"Well, trust me, you're worth it... I don't know what I'd do without you."

The words were out before either could stop them, and Anna blinked several times, realizing how close they were, where his hands were. Her heart pounded in her ears.

They weren't at the event, there was no need to pretend anymore. No reason for him to absently lace his fingers in hers.

_Too close_ , she thought. _Way too close._ Clearing her throat, she instead retrieved her fingers and concentrated on the task of fixing his lopsided tie, then stepped back, appropriating their distance. Meanwhile Jack reached up to rub the back of his neck incessantly, trying to come up with some way to salvage this awkward moment with something witty. She could tell. He had that look. "I'll-uh-I'll see you at the office," she said.

He nodded fervantly. "Yeah. Yeah, I'll see you, then."

He got in his car and drove away.

Anna stared down at the beautiful eight hundred dollar gown that now belonged to her.

She definitely had to do something about this.

It was time she and Jack had that talk she'd been dreading.

* * *

Later, on the other side of town, Jack pulled into the two story garage below his loft apartment, killed the engine and rested his head on the steering wheel, wallowing and moping in pathetic self loathing.

"God, what is wrong with me?" he said aloud, before finally prying himself off the leather seat like a Band-Aid strip and climbing out of the car.

Upstairs he went to climb out of his stifling suit and throw on a Smashing Pumpkins album tee. Then to the freezer to decide if he wanted a whole bottle of Jack Daniels, a whole tub of Ben & Jerry's, or to just slam his head in the freezer door repeatedly until his brain was functioning properly. After an inward debate, he settled on sobriety, and a cold turkey sandwich that looked as sad and helpless as he felt.

All evening long he'd thought about that dance with Anna when he'd almost spilled his guts about how in love with her he was.

How he _didn't_. And how he _should've_.

He knew the cause of his problems with dating, as soon as she'd addressed the issue. He knew exactly why he had such terrible luck with all these shallow, vapid women that seemed to be a mainstay in his life, and why it seemed better just to lie and say he was happily taken, rather than attempt to date. Why he never went out on those second dates, just like Anna pointed out to him. He knew it as soon as he realized how he felt about her.

Because as soon as they opened their mouths, he compared them to Anna, found all the ways in which they weren't anything like her, and fixated on those flaws.

Tonight was a close call that got him thinking.

That maybe it was time to have that talk with Anna he'd been postponing.


	3. All Caught Up

She was jittery even _before_ coffee for a change.

She stood in line at the local cafe, waiting for his, hers, and Evelyn's morning cup, tapping her foot and incessantly brushing her hair back, thinking it over. Her heart felt like it would explode at any minute, and she was just waiting to pull out a clump of hair the size of her fist from all the stress. It wasn't like she could just quit. Not without finding something to fall back on first, and she wouldn't leave Jack without notice.

He deserved at least that much from her.

She was so busy stressing over what she was going to say to him that she didn't notice there was a new car in the garage next to his Audi, when she pulled in and parked her pre-owned Kia. So busy stressing that she didn't notice a jacket laying on one of the chairs in the reception area, and instead marched right up to Evelyn with a smile and removed her to-go cup from the biodegradable cup caddy.

"Here you go, one decaf, nonfat latte for the loveliest receptionist in town," she said and Evelyn chuckled, taking the cup and reaching for her purse to reimburse Anna for the coffee.

So stressed-but trying to hide it-that she didn't notice _two_ men stepping out of Jack's office, instead of one. "Thank you dear," she heard Evelyn say, holding out cash, pocketing the change as she turned around.

Coming face to face with Ron Malenack.

_Shit_.

"Mr. Malenack," she squeaked, then cleared her throat, forcing her pitch back down an octive. Her eyes darted to Evelyn's, then back to his. "Good morning." She glanced at Jack, who was following him out the door, his eyes widening a little in an 'I'm so sorry' kind of way, when Ron wasn't looking.

"And a good morning to you, Miss Baker," was Ron's response, cracking a wide grin. He looked down at the two paper cups in the cardboard tray she held. "Well, aren't you a lucky man, Jack," he chuckled. "Your girl brings you coffee every morning?" He reached for his jacket sprawled across one of the chairs and threw it on. "Now I see why you don't need an assistant. You've got a wonderful caregiver right here."

Jack ran his hands through his hair. "Heh, yeah, see this is why I should've hired her," he fake laughed. "I'd fall apart without this woman in my life."

Anna chuckled. That wasn't fake. That was just plain truth. He would die tragically trying to tie his own shoelaces for a change. She could imagine his obituary. "And with me, you've got the best of both worlds, don't you, _honey_?"

"But of course," he smiled, then checked his Rolex. "But you're going to be late for work, aren't you, _beautiful_?"

For about three seconds, the tension in the room was so thick she could write her name in bold letters in the air. "Why, yes, yes I do," she said, then handed him his coffee. "I'd better get going then. I'll see you for lunch?" She reached up to kiss his cheek, smacking one right on the side of his face. _No harm done_ , she thought. _It's... It's just a cheek, right? This is third grade level affection. It's fine._

"I'm on my way out," she heard Ron say, as Jack turned his head, and... planted a kiss right on her lips, arm snaking around her waist. Breathing was hypothetical for a moment. "I'll walk you to your car," Ron offered.

"T-Thank you," she managed to say to Ron. _Oh my god, he just kissed me!_

Out of the corner of her eye she could see Evelyn's eyebrows shoot up to her forehead, accentuating the lines already there. Ron just smiled and said, "Well, thanks for letting me stop by before my flight, Jack. It was good catching up with you." Jack nodded in agreement. They reached to shake hands, then Ron offered his arm to Anna like the perfect gentleman, saying, "Shall we then?"

She forced the most genuine smile at him and let him lead her out of the office, taking her coffee cup out of the carrier and tossing the cardboard into the waste bin. With her back turned to Jack, she looked over her shoulder to shoot him a wide-eyed questioning look, and saw his expression. Equal terror, mixed with shame and mortification, hand covering his mouth. Out the door she went with Ron and started toward the elevator.

"Do you mind if we take the stairs?" he asked. "My doctor says I should get more excercise, so I get it where I can. Plus, it gives us more time to chat."

"Of course," she nodded, still smiling, and led him to the stairwell. She hated those stairs. Ever since that first day, she was paranoid that some day she would actually fall and break her neck on them, so she did the logical thing and took the elevator. Fighting against the weakness in her knees, both from the stairs, and that kiss, she stepped down beside Ron and settled in to the easy paced companionable descent.

"You know, I have to say, you're even better in person," he told her. "I mean, Debra has been telling my wife all about you for months now, so I feel like I already know you. But the real thing is still quite a treat. Jack seems to adore you. You guys seem right for each other. And he seems so happy."

"Oh, uh, I'm glad," she said. "You know, Jack he's, well, honestly he's the best thing that's ever happened to me. I think I'd fall apart without him too." _Months?!_ she screamed in her head. _Months, Jack?! You've been passing me off as your girlfriend for months now?!_

* * *

Back at the office, Jack wiped the smile from his face as smeared a hand across it. He'd _kissed_ her. Not a light peck on the cheek, but on the mouth, getting a taste of that vanilla chapstick she always wore, the feel of soft, perfect lips against his, and... _damn_. He was a dead man. He didn't even know how it had happened. One second she was there, pecking his cheek, then the next thing he knew, he just... did it.

It felt so natural, so right. He leaned in, she leaned in, and it just... _happened_.

He remembered that Evelyn was there where she loudly ahemed, and he whipped around sharply on his heel. "Since when has _this_ been going on? Does _she_ know about this?" she asked, eyeing him quite disapprovingly. Then her eyes widened. "Don't tell me you're cheating on your girlfriend with your assistant!" she gasped. "You're having an affair? Your mother is going to-"

He rushed to her desk. "Wait, no, no, Ev, Anna..." He scrambled for the second that it took his brain to catch up with his mouth and connect the two. "Ev, Anna... _is_ my girlfriend," he said. "Well, that's not... I mean she _isn't_. But, well, she _is_. Anna is the one I've been seeing. Well, she's pretending to be. But we're not seeing each other." That made _zero_ sense. He floundered. "You know how mom gets, and Anna... It's just-"

"Ohhh," she said in sudden realization. "Oh, so you mean _Anna_ is the girl she's been telling me all about."

"Yes," he nodded emphatically. She opened her mouth to speak. Then he held up a finger in warning. "Ev, I _swear_ , if you tell mom that Anna is my assistant, I'll," He grasped at straws for a moment, "You can forget about your Christmas bonus," he came up with, and Evelyn scowled. "Just don't say anything. Please." She grumbled a little, pouting, before swiveling in her chair and turning back to her computer.

Jack trudged back inside his office to collapse in his chair. Staring up at the ceiling, he contemplated his stupid decision to ever propose that Anna pass off as his girlfriend. But he knew how much it would make his mother happy to hear he'd finally met the right one, that he might finally settle down, and Anna... Well, Anna _was_ the right one. It was just that Jack-and Ron Malenack-had terrible timing.

* * *

On their way out the building, Anna felt her pocket vibrate, and checked to see the text from Jack, saying, 'I'm so sorry.' _Yeah, I bet you are_ , she thought, pocketing her cell and shooting Ron a smile. When they entered the parking garage, she had the plan in her head to wait for Ron to leave first, then hide in the garage until he was at least a block away, before she headed back up to the office.

Then she was going to tear Jack a new one for this.

But every other thought left her head when Ron stopped at the rental car next to hers. A brand new, off-the-lot, polished and gleaming BMW, pulling out his keys to disengage the alarm. But he had paused when he got a look and her delapidated vehicle beside it. He chuckled, shaking his head. "You know, it only makes sense," he said, and she furrowed her brow, confused by that. He gestured to her car.

Then he said, "You know, way back when, I could remember Jack's father always talking about his son, how he had such high hopes for his boy." Her heart fluttered. Expecting some sort of insult. "He wanted to give him everything. All through school, he was always right there to pick Jack up if he fell off the wagon. Had a job lined up for him, and we all thought Jack would take over the business one day. He even offered to pay for college."

He leaned against the hood of his BMW and folded his arms. "But you know what was so funny about Jack was... Well, he could have whatever he wanted, but he was determined to make it on his own. Wouldn't take his job offer, wouldn't take his money. Accepted a scholarship instead. Worked two, sometimes three jobs to hold it all together, then flew across the country to make his own way. Make his own life, right here."

Anna didn't really know what to say, so she just nodded at that.

"Everything he's got, he's earned. And I think now I understand why he's with you," he said. "You're smart, educated, independent, and you remind me of him," he smiled. "I just hope he earns _you_ ," he laughed, and so did she. "You know, I never got the chance to ask, how did you two meet?"

"Oh, well, uh..." She fiddled with her keys. Then she chuckled a little. "It's actually kind of funny. He was... interviewing me for a job," she admitted. "I... had the worst day that day. My lipstick broke, my cab driver overcharged me, I was running late, almost broke my ankle on the stairs, my shirt was missing a button, and..." She sighed. "I was literally falling apart at the seams," she laughed.

"...I stumbled into the office to see two _gorgeous_  women almost half my age waiting to be interviewed, and I thought Jack was one of _those_ guys. I'll be honest, I thought he was a shallow, conceited jerk looking for a hot, easy date, and I screamed at him, called him a chauvinistic pig, the whole nine yards." Ron gaped a little at that. She nodded and said, "No joke, I _really_ let him have it, then I left."

"You left?" he repeated, and she nodded.

"I did. I thought to myself, _I want nothing to do with this guy_. But the funniest thing happened. He... well, he _chased me down_ , nearly tripping over himself. Swore that he wasn't the kind of guy I was thinking he was. That Evelyn was the one who scheduled the interviews. That it was a coincidence. And then he..." She paused. Flashing back to that moment he came running down the stairs, out of breath, slid across the tile, tie crooked and everything.

Her heart hammering in her chest.

Like a man that simply couldn't live without her.

"... He asked me out," she lied. Ron smiled. "And, well, I said yes, of course. I settled for a job at another company, Jack settled for me. And we've been stuck with eachother ever since."

"So you gave him a chance, did you?" he asked.

"Well, he seemed pretty determined not to let me get away. And I knew-" She swallowed. "I knew I couldn't let him get away either."

"Well, I'm glad," he said, reaching to pat her shoulder before he opened the door to his car. "It was really great meeting you, Anna. I hope we see each other again soon."

"Meet too," she said, with a genuine smile, then watched him drive away. She stood there for a while, feeling ashamed for lying to the man. And a moment longer, feeling disappointed. She never knew that about Jack, that he'd forgone any assitance from his family, that he'd worked hard to earn all he accomplished. She was very proud of him. But then she remembered how he'd lied about dating her, and she flexed her jaw.

She was fully loaded, and ready to go about chewing him out by the time she reached the office floor, masking her emotions behind a blank look when she passed by Evelyn-who said nothing-then barged into his office. He looked pretty pathetic when she walked in, slouching in his chair, but sat up abruptly. "I'm so sorry," he said, as she stalked over to his desk. "I didn't know Ronnie would stop by, I mean, he didn't call first, so-"

" _Months_ , Jack?!" she huffed. "You've been passing me off as your girlfriend for _months_?! Exactly _what_ did you tell your mother, Jack Bartlett?" she demanded, and he froze, looking like a kid with his hand halfway in the cookie jar. It clicked in her head suddenly. "Oh my god, Jack, you didn't just lie to her about being in a relationship, did you?! You didn't just make someone up! You told her you were dating _me_! What the hell!"

He slowly rose from his seat, hands in the air like he was being held at gun point. "Okay, heres the thing," he said slowly. "When I said I lied, I just meant that I-" She huffed again, folding her arms.

"Don't you even dare give me any bullshit," she scathed. "Start explaining."

"I didn't know what else to do!" he whined, flailing his arms. "She started asking all these questions, and I didn't want my answers to sound fake, I wanted it to be believable, so I... I started describing _you_." He gestured to all of her. "I figured if I was telling her about a real person, then I would never get my facts mixed up. She..." He sighed. "She sounded so happy for me, I couldn't tell her the truth."

"You _need_ to, Jack," she said, and he started stepping around the desk.

"You know I can't do that, Anna," he said. "You know how she'll react. And she's so excited, I mean, you should hear her on the phone. She's so happy her son's finally found the right one, someone who's smart, funny, gorgeous, and isn't trying to clean out my bank account. If I tell her the truth, it will break her heart, or worse, she'll think I did something to mess things up between us, and she'll never let me hear the end of it."

"Well maybe that's what you deserve for acting like such a child, Jack," she told him. He gave her the wounded puppy look. She fiddled with her skirt for a moment. It was hard to stay mad at him whenever he made that face. "You really told your mother all that stuff about me?" she asked, and he nodded. "Did you happen to mention to her that I'm your assistant? And that I already have a boyfriend?"

_Oh shit_ , she thought, _Tim. I'm in a relationship with Tim and I kissed my boss._

_Oh my god I'm such a whore_.

"I didn't mention those things, no," he said. "I'll... I'll just tell her we're breaking up. That things aren't working out, and... It stops here."

"Good," she nodded, and then it got awkward. Neither knew what to say after that.

She was warring with herself over whether she should just walk out right then and there, quitting her job, sacrificing her cushy salary, and possibly her friendship with Jack. It wasn't like he couldn't replace her, but no other person would ever tolerate half his behavior. And could they be friends still, if she quit her job? Could they still go out for midnight coffee? Split sub sandwiches? Or would that change if he got a _real_ girlfriend?

And Tim. What was she going to say to Tim? Or should she tell him at all? It wasn't like she did it on purpose, that she actually cheated on him, intentionally. They didn't feel each other up in the broom closet or anything, they just... _Dammit, now I'm picturing the two of us in the broom closet!_... No. No, she just... got caught up in the moment. So did Jack. It meant nothing... right?

"Well, I guess we should get to work," he said. "And I suppose I have a phone call to make. Wish me luck."

"You know," she started, making him pause. "Maybe you don't need to call her... _right_ this second," she said. His eyes brightened a little, as if to say, 'Really?' "I mean, as long as Evelyn can keep her mouth shut, it can't hurt to wait."

"Well I took care of Evelyn," he said. "Nipped that in the bud. Mum's the word."

"Okay, good," she nodded. "I'll just..."

"Do you... plan on telling Tim about this?" he asked, and she chewed her lip.

"I don't know yet," she said. He nodded a little, but his expression was too unreadable for her to guess whether or not he was happy about that. She knew he didn't like Tim anyway. So maybe he wouldn't really feel all that terrible if what they did ruined her relationship. They dropped the subject, set everything aside, and went through their routine like clockwork, Jack starting on the Barnes-Adams case that would go to trial.

While Anna got Jack through his day, she was busy mulling over a thought that stuck in her mind that morning. The sudden realization that throughout all that... Talking to Ron, having it out with Jack... Dealing with Tim had been the _last_ thing on her to-do list. In fact, all she could think about was Jack. She'd never really considered _Tim's_ feelings, or how badly she would hurt _Tim_ if the truth came out. Instead, she'd been so caught up in Jack.

And that kiss they shared. It just felt so... so _right_.

* * *

Things were weirdly professional between them that morning, and it drove Jack nuts. The way Anna made it a point to be stiff and formal with him every time they spoke. She still used his first name, but no nicknames. No Champ. The only thing even remotely personal that passed between them in conversation was, "So you want to go out for lunch today?" Which was followed up with, "Sure, sounds good." But that was it.

He'd gotten so used to their usual back and forth that without it, he felt like his entire world had tilted on its axis and winter was summer. But it opened his eyes to how comfortable they'd become with one another. Made him realize that maybe they were _too_ comfortable with each other. Maybe she was realizing this too. Maybe this was how it would have to be from now on. Stiff and rigid. Boring and quiet.

He HATED it.

They walked in the most _excruciating_ silence to the 24 hour diner a few blocks down where they served breakfast all day, and the best burgers in the city, by his and her unanimous vote, sliding into their usual booth. And per usual, Anna ordered the two-for-one special for them; two burgers, one with extra pickles, heavy on the ketchup and mayo, one with no pickles, but with lettuce, two orders of fries, one diet Coke, and one regular Coke.

"Please," she added at the end, and the waitress blinked, before she remembered she was supposed to be writing everything she rattled off down on a slip.

When the food came, per usual, both orders of fries were dumped in the middle of the tray, both picked up their drinks, sipped from their straws, and winced at the taste. Drinks were backwards, so they switched, and per usual they picked through their food, Anna weeding out the pickles accidently added to the wrong burger and piling them on the other, grumbling under her breath about aspartame.

He handed her extra napkins, and she passed him the salt.

The waitress, who was new, tall, blonde, and had been watching this, asked how long they'd been going on. Anna smiled tightly and said, "No, I'm-I'm not his girlfriend. I'm just his assistant."

"Oh," she chuckled. "It's just... you guys look you know each other pretty well," she said. Then she skirted away, smiling and biting her lip a little at Jack on her way past his seat, but he didn't notice. He was too focused on the way Anna was scrunching up her face in consternation to care that the waitress might've been checking him out, and clearing the channels, seeing if he was actually taken, or might be single and available.

According to his mother, he was neither. But according to his pretend girlfriend, he might be pretty soon. If they were _really_ dating, this would _definitely_ be the awkward silence before a break-up. Without looking up from her meal, Anna held out her hand, saying, "You'd better hand over the wallet and let me pay the check. That woman is _definitely_ going to flirt with you for a bigger tip." He sighed, rummaging through his pocket for the billfold.

Handing over what could've been a victim to a serial blonde, but was now in the safety of Anna's loving hands, Jack summed up what he wanted to say to her, fully prepared to have that talk. But he didn't get the chance to speak. Anna took his wallet, setting it on the table beside her, and stared at it for a second before sighing, then said, "Jack, I think we need to talk about what happened."

"Uh," He scratched his head, "Okay? Shoot."

She set down her drink and sighed, finally making eye contact. "Is... Is there... something between us?" she asked, and his heart started racing.

"What if... there was?" he asked, and she processed this. Did that thing with her bottom lip that she did whenever she was conflicted about something. "I-I mean is... Is it weird? The idea of... _Us_? Us being together, I mean."

There was a stretch of silence, before the ball dropped and she said, "Listen, Jack, I really like my job. I don't want to quit. I don't want to put either of us in that kind of position. I mean, me hunting for new employment, you searching for a replacement, all that-" As she was speaking Jack felt his whole world fall out of orbit entirely. He always thought that would happen if she _quit_ , not the other way around. "-I don't want to-"

"Don't quit," he rushed to say. "I don't want you to either. Not if... I mean to say I just... If you're happy with the way things are, then so am I."

"Well... I _am_ ," she said, but the way she said it sounded more like she was telling herself that. "I mean, I _am_ happy with the way things are. And I'm... I'm happy with Tim."

He nodded a little. "Okay, yeah, sure, I'll just-uh... I'll see you back at the office then," he told her, reaching across the table to snatch up his wallet and head to the counter to settle the bill. She didn't even try to stop him. He approached the counter to see the tall, busty blonde that had served them, and ground his teeth for a second before she looked up and he quickly put on a smile. She smiled, leaned forward and said, "Everything good, sweetie?"

The whole five minutes of this woman's company were swimming in his head.

Pretty, but wore tons of make-up, spent too much time checking him out to bother to get their order right. Never apologized for switching their drinks, nor did she offer to take the food back and correct their order. Smacked her gum when she talked. Checked his wrist for a ring, spotted a Rolex, fished around to see if he was single, batted her eyelashes, chewed her finger nails... Dammit, Anna was right. He inwardly sighed.

He never gave women a second chance, did he?

He mentally drop kicked them after their first impression.

Well, maybe it was time to suck it up, forget about Anna, and give somebody else a shot.

He stepped up to the counter.

"Hey, so are you... free tonight?" he asked.


	4. Wipeout!

"Just what is so funny?" Anna asked Linda, when she burst out laughing, loudly, spilling her cocktail. Tears streamed down her cheeks, and Anna sulked, slumping her shoulders and hunching over her half-priced special.

She didn't normally go out for drinks, and usually much preferred to stay home on the weekend and enjoy a good book, but she needed this after the fiasco with Jack. So she caved, and one cranberry vodka into the night, she spilled everything about the fake dating, telling Linda the whole story. Everything from the charity ball upstate, to her conversation with Ron in the parking garage, and Jack's bad decision making skills outside of court.

Linda wiped her tear streaked face and said, "I don't know what's more amazing, the fact that you can scream at your boss like that and get away with it, or how clueless you are to the universe sending you a sign that the man's got it bad for you." Linda sat back in her seat. Anna rolled her eyes. "I mean, seriously. He tells his mom how perfect you are? How he's finally found the right one?"

"He just said all that to make her happy," Anna argued, not willing to believe that Jack maybe truly felt that way about her.

"Yeah, but of all the people he could've picked out of a line-up, he picked _you_. He describes the perfect woman and _your_ name falls from his lips. And then, he offers to make your fake relationship the real deal and you _keep_ your job? That's basically crapping on the universe's billboard here." She tipped back her glass and drained it. "I don't understand why you didn't just quit."

Anna sighed, and fiddled with her glass. "I can't leave him, Linda, he needs me. And everything would change if we started dating. I mean, I know how he is. I know the good, and the bad. And I know how he can be with women. It's like his brain shuts off and stops working. Sometimes, I don't know if I could be on the receiving end of that. And what if things didn't work out between us? What if it's a waste of time?"

"You really think it would be? You, my friend, have some serious issues. You really need to-"

"Oh shit!" she breathed, eyes widening, when she saw _Jack_ walking in the bar. With a _date_. "Oh my god, it's him," she said, tapping Linda's arm, and she peered around the booth to see. "He's on a date. And he brought her _here_. Oh my god he actually brought somebody _here_." She hid her face with her hand just in case he might notice her. "Stop staring," she hissed at Linda. "He can't know I'm here too. It'll ruin everything."

"Oh, honey, he's... wow, you're right, _he is gorgeous._ Oh my god, the things I would let that man do to me-"

"Linda!" She smacked her arm, and Linda mouthed an 'ow'. "He's my boss, remember?"

"Yeah, and boy are you stupid," Linda chuckled. "There is no way I'd pass up the chance to sleep with that hunk of meat right there, but _somebody's_ about to."

Anna peeked, and caught sight of the waitress from the diner and scowled. She was dressed in a skin tight little black dress, with matching black stilettos, and rubbing his leg with hers under the table. A creep of jealousy rose up her spine, and she bit the inside of her cheek. _She is so totally not his type,_ she thought. _Any minute now he'll be calling me for a bail-out_... But what if it was real? What if this one turned out to be a winner?

"Hmph, you're right, he is cheap though. He takes her to a place like this?" she heard Linda ask.

"Yeah that's how I know he's serious," Anna told her. Linda gave her a funny look. Anna sighed. Then explained. "When he's not serious about a woman and just looking to get laid, he lets them pick the place, and lets them order whatever they want, even picks up the check. Sometimes takes them to the most _expensive_ restaurants, because he doesn't want to make them feel like they're cheap. Which is why I have his credit card."

"He gave you his credit card?!"

"Yep. If I don't hold it hostage, he'll max it out, get behind on the payments, and sink his credit score. All because he's trying to impress his date."

"Huh, so he's _not_ cheap then," Linda said, with an air of surprise.

"Oh no, he _is_. Believe me, he's cheap. If he's _seriously_ interested in a woman, he takes them to places like this."

"Why?"

"To see how they react. To see if they'll get offended by being taken to a low-key, reasonably priced venue because he's so inexorably cheap. Sometimes he doesn't even tell them what he actually does for a living, or lies about his profession. To see if they're actually interested in him, or after his money." Linda raised a brow at that. "But if things  _really_ get serious he goes all out, and loses his mind. Money becomes no object."

"Okay, so...  _he's_ the one with psychological issues then," Linda surmised, and Anna clucked.

"No. He's just... way too nice."

"Sounds to me like the guy's off his rocker, honey," Linda huffed. But Anna detested the assumption.

"No, he just doesn't know how to handle sophisticated women. His idea of a date is talk, get to know one another, or do something like see a matinee at the theater, or burgers at the diner. Places like this, or ice cream at the park on a Saturday afternoon. Not clubbing or bar hopping. _Definitely_ not singles bars. And he goes home alone. He won't even sleep with a woman on the first date. That's his rule."

"Wow so he's every earthly woman's dream date," Linda derided. "And a tightwad."

Anna rolled her eyes at Linda's reprisal of Jack's romanticism and studied his date. "I don't know about this one, she's not his type."

"And how would you know?" Linda asked, curious. Anna shot her a glare, scooting forward in her seat to get a better vantage point.

"Because according to you, _I'm_ his type," she glowered, disdainfully, then shifted her eyes back to the scene before her. Reading Jack's body language and grinding her teeth.

* * *

Mercedes, as in the _person_ , not the _car_ , had given him a curious look when he asked to meet her here. Not really disgust, nor was it confusion, but just a quirky lift of a brow. Not really much to go on just yet. But at least she didn't question where he picked for their first date. When they sat down at the table she looked around and said, "It's... so quaint," with a quick flash of a smile.

He smiled winningly back at her. "I love this place," he said. "I used to work here back in college, and it brings back a lot of fond memories. It's kind of special to me."

"Oh," she chirped. Then she leaned forward, elbows on the table, smiling and rubbing his leg with hers. He jolted a little, as he wasn't expecting the contact, but tried to shift back into a more relaxed pose. "So... what do you do for a living?"

 _Why is that always a woman's first question?_ he thought.

Why not ask him what he liked to do for fun? Where he went to college, or if he likes sports?

"I'm-uh-I'm in sales," he said. She mouthed an 'oh'. "It's... well, it's not much right now, we've kind of hit our slow season." He shrugged. "Kind of got behind on my rent, but you know how that is." Her lip twitched. But she wasn't backing out of the pool just yet. She reached for his hand on the table, smiled and bit her lip. "So you-well-I saw you at the diner, so I guess I already know your profession," he shrugged.

"Uh, well, uhm... I actually got fired today?" she said, starting to twirl her hair with her finger. "Apparently you're not supposed to hit on the customers," she giggled.

"They fired you just for flirting with me? I'm so sorry."

"Oh, it's ok. I was already on my third strike, so..."

"How long did you work there?"

"Uhm," She stared up at the ceiling like she was counting a really big number, "Like, a day," she said. 

"Just-just one?" he asked, and she nodded. "Okay, so uh, what do you like to do, Mercedes?" he asked, and inwardly groaned at the answer.

"Hmm, what _don't_ I like to do," she purred suggestively, waggling her brows, then giggling. _Geeze, lady, were you a hooker?! I'm trying to have a conversation here!_ he thought.

She continued touching him, and the more she touched him, the more this odd sensation creeped down his spine. He felt like he was _cheating_. It just felt all wrong. She was beautiful, but the way she was coming onto him, it just didn't feel natural. And in the back of his mind he was still thinking of Anna. The way she felt when he slid his arm around her waist, the way her lips felt. Wondering what it would feel like to make love to her...

This was all wrong, and he knew it. Here he was, on a date with a woman, but getting turned on thinking of someone else. He should've told her the truth from the start. He felt pretty terrible about that. He was starting to lose focus, spacing out, thinking about all the alternative ways their conversation could've ended, and not even paying attention to Mercedes The Person anymore.

 _God what am I doing?_ he thought. _What was I thinking?!_ Then he reached for his phone, leaning back in his seat. "Oh, I just remembered. I'm so sorry. I forgot to text my partner and tell him I won't be coming into the office tomorrow." Mercedes The Person perked up in interest. "Gonna be a late night," he winked at her, and she practically bounced in her seat, thinking she was going to get lucky. "Just give me a few."

He cursed himself for what he was about to do, but after weighing his options he realized he was about to make a mistake. The last thing he needed was to accidently say Anna's name in bed with this woman because he couldn't get her out of his head. So he flashed a smile as he text Anna under the table. 'Please help me before I do something really REALLY stupid,' he sent, and waited for a reply.

* * *

Linda glanced down at her phone when it vibrated on the table, arching a brow.

They had both seen him act liked he'd forgotten something, make apologetic gestures to his date, then text someone.

"Is he... is he texting you on his date?" Linda asked, and she checked her phone. She rolled her eyes when she saw the message. She saw it coming a mile away.

"Yeah," she told Linda. Then she text, 'I'm not bailing you out again.' Seeing a flash of fear dance across his face as she watched him read the text, then glance up at his date, who was still smiling at him. Then his eyes darted back to his phone, and he furiously typed, 'Please, Ann, I think she was a hooker', making her snort. "He texts me when he thinks the date's about to go south and has me bail him out."

Linda chortled. "So what's wrong with his date?"

"Coming on a little strong," she said. Then she typed, 'Just tell her you're not interested.'

'Too late, she thinks I am.'

'Boy, you really wedged yourself in deep this time, didn't you?'

'PLEASE.'

'NO.'

He all but spilled his drink. Anna was starting to crack up at the little lost puppy face he was making, starting to realize he would have to handle this one his own, and meanwhile his date was edging closer and closer until she was practically in his lap. 'Come on, you can do it, big guy,' she sent. 'You've got this.' She showed Linda the text and watched her cover her mouth when she snorted with laughter. "Oh, just cut the guy a break," she said.

"No," Anna shook her head. "He needs to do this."

"Oh come on, look at him, he's squirming."

'It's like a bandaid, Jack. Just count to three, and pull.'

'Oh haha funny,' he text as he edged away uncomfortably from Hooker Barbie. 'Please, Anna, I swear I will never ask you to do it again.'

'You promise?'

'I promise. Because I think after this, I'm changing my name to Mary Louisa and joining a convent.'

She burst out laughing, and then saw Jack furrow his brow.

He shifted his eyes to the side, and saw her. She winked. Linda leaned over and waved. He scowled at both of them, but his date hadn't noticed them, and she got an idea. 'Alright, fine. But prepare for the bailout of a lifetime, Champ.'

* * *

As soon as he heard Anna laughing on the other side of the bar, he knew he'd been had. She'd been there the whole time, watching his date, and was screwing with him. But at least she was back to her old self, and they were back to their typical quirks. He was flooded with relief when he saw the word Champ come across the screen and knew she wasn't upset with him anymore.

He braced for whatever was coming, but he couldn't predict what was about to happen.

Mercedes was clueless in her seat, biting her lip, twirling her hair, and giggling still, when Anna strode right up to their table, surprising the hell out of both of them. "Jack?!" she shrieked, as if she didn't expect to see him there, and he jumped, spilling his drink down his shirt.

"Anna!" he exclaimed, reaching for a napkin.

"You're cheating on me?!" she shrilled, and Mercedes' eyes widened.

"You're sleeping with your assistant?!"

"How could you do this to me?! I thought you loved me! And to think I was going to marry you! Well, guess what, I quit!" She splashed the drink she was holding in his face after he'd only just managed to wipe up the spill of his own. He sputtered for a moment. But the object of his desire was not finished yet. No, there was more. Anna's friend Linda walked up to their table. He recognized her by the way Anna had described her.

"Jack?!" she also shrieked.

"Linda?!" he exclaimed right back at her.

"You're cheating on me?!"

"Oh my god, you're screwing her too?!" Mercedes hitched, at the double whammy. She glanced back and forth between both women.

"Who the hell are _you_?" Anna asked Linda.

"I am his _wife_!" she proclaimed, and Anna faked shock, but Mercedes' was genuine.

Perfectly timed, they both gaped in shock at Jack and chimed, "You're married?!"

"I want a divorce!" Linda snapped, and Jack braced. Yep, she splashed her drink in his face next. Mercedes stood up from the table.

"I can't believe this!" she huffed. "First you take me to some crummy bar, then you're sleeping with your assistant, and then you're married too?!" She scoffed in disgust. "And to think, I was going to let you get lucky tonight. Have a nice life."

And then came drink number four. She grabbed her purse and stormed out, both Anna and Linda watching her leave, and Jack was soaked, sputtering and spitting, shaking his hands dry. He glanced up at both women, who grinned victoriously at their feat. "You're welcome," Anna purred, and he nodded lamely.

"Yeah, yeah, thanks," he returned, and Anna plopped down in the now empty seat across from him. Linda leaned against the nearby table divider. "Nice to meet you, Linda," he said to the woman, who nodded, toasting him with her empty glass.

"So, are we going to break up with our own dates, from now on?" Anna asked, using baby talk, and he scowled.

"I was serious about the convent thing, but with you two, I might just have to leave the country," he smarted, and Anna chuckled.

"Well, that was fun," said Linda with a sigh. "I can see why you kept your job. I'll see you later, sweetie," she told Anna and walked away.

"Night," Anna called after her, then turned to Jack. "You see that? I bail you out, then she bails on me," she told him, jerking her thumb at Linda. "Oh, honey you're _soaked_ , I'm so sorry." She got up and scrounged for napkins while he stood and peeled off his jacket, pausing for half a second when she called him 'honey', but then shook the thought from his head. She probably didn't mean that the way he _wanted_ her to mean it.

"What were you thinking bringing a girl like her to a place like this?" she asked as she helped him dab his shirt with napkins. He chuckled at the irony. A cheap date brought to a cheap establishment. "You know what your problem is? You're too much of a romantic," she told him. "It's like you think the perfect woman is just going to waltz into your life, and it's all just going to come together like magic."

He shrugged. "Worked for my parents," he said. "And you," he added.

She lolled her head. "Being perfect as your assistant isn't the same thing as being perfect for _you_."

He sighed, thinking how his night should've just started and ended with _her_ , because she _was_ perfect.

But he couldn't come up with anything that wouldn't drag back up what happened between them, and make things awkward, so he neglected to respond and instead asked, "Weren't you supposed to be going out with Tim tonight?"

"Oh uh," she slowed her movement for a bit. "Well, he got invited to a game with some friends, and he knows I'm not really into that sort of thing, so we just rescheduled."

"He cancelled dinner with you for a football game?!" he asked, in disbelief. She rolled her eyes.

"He doesn't get to go out with his friends very often, and what kind of girlfriend would I be if I didn't let him do the things he likes to do on occasion?"

"Yeah? And what kind of boyfriend is _he_ when he seems to only come around when he _wants some_?"

She scowled at him. He'd toed the line. "My relationship with Tim is my business, Jack," she snipped, clutching his collar. "But for the record, no, actually, it's _not_ just about sex with Tim."

"Oh really? When was the last time you two went out?" She looked down, and angrily fixed his tie. She took way too long to answer, but he knew she hated being wrong about something, just as much as he did. He sighed. For her sake, he could be wrong, just this once. "I'm sorry," he said. "You're right, it's none of my business. I just think you could do better than this guy. I don't like seeing you get hurt, Anna."

She smoothed the wrinkles in his shirt and nodded a little. "Well, I appreciate that. And trust me, if I ever need a bail-out, you're the first person I'm calling."

He could live with that. "Do you need a ride home?"

"Oh, uh, no, I was just going to call a cab."

"You sure?"

"Yeah, I'll-I'll be fine, Jack." Absently she reached and brushed stray hairs from his face that were soaked with alcohol still, but she didn't seem to care. "But you," She tapped his chest, "You stop bringing hookers to bars and join that convent, you here me?" He laughed at that. She smirked up at him. That same sly curve upward that she gave him when they first met, that he'd been addicted to ever since.

That smile. It was worth everything. He'd trade everything he owned to see that smile, but if only he could tell her that. "See ya around, Champ," she told him.

"Night," he said as she walked away.

* * *

She flopped down on the sofa as soon as she was inside her apartment and sighed.

 _Why am I doing this to myself?_ she thought.

But she didn't have much time to dwell on her current existence, because the lock on her door jiggling made her jump. It was Tim, coming through the door with his recently awarded copy of her key. "Hey babe," he said, smiling, when he saw her.

"I thought you were going to the game?" she said, getting up from the couch and walking over to him as he was taking off his jacket and hanging it on the hook.

"Yeah, about that. Something happened with the tickets, so... I was thinking," He slipped his arms around her waist and pulled her in for a kiss, "That maybe we could watch the game here tonight?" he asked, then kissed again, this time on her neck.

"Oh, uh... sure, that sounds... That sounds great," she told him, absently thinking to herself how droll it was going to be to sit through a football game, but at least they'd spend their time together, curled up on the couch, which sounded nice. Sounded like something couples did together. And they were a couple, right?

"Great," he said, then backed away. "Oh this is gonna be awesome." He walked back out the front door and shouted down the stairwell. "She said it's alright, come on up!" She blinked in surprise when four men came barging in and huddled in the living room, settling on the couch and pulling up chairs in front of the flat screen. "Thanks babe!" he called to her from the couch, and turned the volume up. Well, she hadn't seen _that_ coming.

She sighed and walked into the kitchen, setting her phone on the counter and cracking open the fridge. "Yay I'm stuck with five jocks and a half eaten casserole," she muttered. She closed the fridge and peered around the doorframe at the crowd of men in her living room. Well, Jack was wrong about something. It seemed their relationship truly wasn't just about sex, but apparently it was about her _flatscreen_ too. She scowled.

She honestly didn't think starting a fight with Tim just for bringing his friends over to her apartment was worth the hassle. It sounded stupid, the longer she thought about it. So she hid in the kitchen with her cold casserole, fork in one hand, cellphone in the other, scrolling through her messages when a new text from Jack popped up. She almost didn't want to respond. 'You still up?'

She leaned over the counter to see that Tim was enthralled by the game. 'Wide awake', she texted him back. He responded with, 'Coffee run?'. "Hey babe!" Tim called. "Can you make us some nachos?" She slumped for a moment, inwardly debating. 'Meet me at the overpass?' she text, and his repsonse was, 'I'll see you there.' And her heart skipped. It was just coffee at their hangout. Why did she feel like she was cheating on Tim?

"Yeah, I uh, I gotta run to the store, though," she called to Tim, making her way into the living room. "We're out of chips."

Without taking his eyes from the TV, he said, "Okay. Hey, can you pick up a case of Bud Light while you're out? Oh and some Cheetos. Thanks babe."

"You're welcome," she mumbled, grabbing her purse, and her keys, before slipping out.


	5. The Reigning Champ

**Notes for the Chapter:**

> If you are a Mercedes and also a person, I'm sorry. However, if you are a Mercedes and you are a car? Where can I buy you? Because I need a car that reads AO3 fiction in my life. Pronto.
> 
> Also, yeah.

The overpass was a tradition spanning the entirety of their friendship, that happened completely by coincidence.

It started the day they met, when Jack hired her, sent her off to go shopping for appropriate office wear that didn't have missing buttons, and pick up lunch from the diner (their two-for-one burgers with fries and Cokes) with his credit card. They ate in his office and talked. About everything. Jack spilled ketchup, and Anna offered to take his shirt to the drycleaners. Both had forgotten about his credit card that day.

But she remembered that night. So she called him up on the phone to return it, and Jack drove to her apartment. Or... _almost_ to her apartment. He had forgotten to take his car to the garage for maintenance earlier that week, and it broke down. She called AAA, and met him under the overpass where he was stuck, to return his card. She brought coffee, and they waited for the tow truck. Sat on the roof of his car and split a pack of M &Ms.

Anna learned two things about Jack that day. One, that he was absolutely a wreck, just like her, and two, that he was _perfect_.

And the tradition stuck with them ever since.

Whenever neither could sleep, or either one of them had a bad day at the office, and sometimes just for no reason at all, they'd meet in that spot under the overpass, have coffee, and split a pack of M&Ms. So that night, Anna sat beside Jack, popping candy in her mouth before taking a sip from her cup, after telling him about Tim inviting his friends-that he had yet to introduce her to previously-over to her place to watch the game.

"So," he said, "You have four strange men in your apartment."

"Yup," she chirped. "That's some women's dream come true, you know. Provided any of them actually plan on sleeping with her." He snorted. "I don't know, Jack," she sighed. "Okay, yes, I'm kind of pissed that he would do that to me, but come on... I don't think it's really worth breaking up over. He just wants to hang out with his friends, that's all. It's just a football game, I mean, it's not like he's _cheating_ on me."

Jack made a noncommittal shrug of the shoulder, and made that face he made whenever he was about to argue the point. "No," she shook her head. "He's not cheating on me. Tim's not that kind of guy."

"Yeah, but how do you really know _what_ kind of guy he is? You've only been going out, what, a few months now? And you only just recently gave him a key? You've _still_ never seen his apartment, nor have you met any of his friends, until tonight? Has he introduced you to his family? No. You know so little about this guy's life, Ann, only what he gives you in small increments, like he's got something to hide."

"We're taking things slow," she said.

"No guy moves _that_ slow," he told her, and she rolled her eyes. "I deal with guys like Tim on a daily basis, trust me, I can smell trouble a mile away."

"Okay, yeah, maybe with your clients, or in a court room, Jack, but everywhere else, you're as clueless as they come," she laughed. "Seriously, what was up with Diner Debbie tonight?"

He sighed. "Ah, yes, _Mercedes_ ," he said. "With cushy leather seats, and a _wide_ open throttle, apparently."

She snorted. "A woman with more mileage than my Kia, I'm guessing?" she asked. "With one too many previous owners?"

"Well, let's just say, I highly doubt she's mint," he quipped, and she laughed. Then he shrugged. "It just didn't feel right," he told her. "I tried to take your advice, and give somebody a chance to be better than their first impression, so I... I don't know what I was thinking assuming it could be her though. And now one of my favorite establishments is forever tainted with the memory, I'm afraid."

"Oh," she groaned, patting his arm in sympathy. "There will be others, I'm sure."

"Yeah, dates that are so bad I forget all about that experience," he groused.

They both sighed. Neither one of them knew what they were doing with relationships, did they? She mulled over everything Linda had told her, and every conversation with Jack, every unplanned surprise visit by Tim, all of it, wondering how she could be so unlucky as to date a guy that didn't really seem to be on the same page, and be stuck working for a guy that got her completely. Was Linda right? Had she made a mistake keeping her job?

She thought about how Jack would fall apart without her in the office every day, and squirmed a little in her spot. That was also part of her problem. She was too focused on Jack's life that she was neglecting her own. And where was she? On the roof of a car with Jack, chuckling as he tossed an M&M into the air and caught it in his mouth. A closet romantic that was addicted to greasy burgers and aspartame.

The occasional car whizzed by, booming on the highway over their heads, but all in all this part of town was quiet this time of night. It was always the perfect escape from their lives. Jack shed his pressed and cleaned suit for a t-shirt and a windbreaker, and shed his persona of crack-shot lawyer for lonely heartbreaker. Anna traded her pencil skirts and button up blouses for jeans and a tank top, and forgot all about her troubles for a little while.

"I should get going," she said after a time, "I told Tim I'd be stopping by the market to pick up some things."

"Why didn't you just tell him you were going out for coffee?" he asked.

 _Because I didn't want Tim to know I'd rather hang out with my boss than him and his sweaty jock straps_ , she thought.

"I didn't want him to think I was upset with him," she said. "Because really I'm not-I mean-I shouldn't be. It's just a game. We'll always have other nights to hang out."

Jack ground his teeth a little. "Okay, well, I'll be seeing you then."

"Alright," she nodded, and slid off the roof. "See ya, Champ," she smiled up at him, and almost melted at the smile he gave her in return.

* * *

"So, let me get this straight," Mark began, leaning forward his seat, perching his elbows on his knees, lacing his fingers together, across from Jack, that following Monday, in his office.

Anna had stepped out to make a trip to Office Depot for-and you guessed it-office supplies. It was no coincidence that they would just so happen to run out of ink for the printer, paper for the fax machine, or need another bottle of window cleaner, whenever Mark made a visit. Luckily, she'd only ever buy something if they _actually_ needed it, but she would peruse the storefront until Jack sent her a text saying, 'Coast is clear.' Then she'd return.

The day she met Mark, he hit on her, and asked her out, but seeing as Anna had the same shortcoming as Jack, she couldn't tell him no. She could never get a handle on rejecting Mark, so instead she made the excuse that Jack needed something for the office and dipped out. Eventually Mark picked up on the subtle rejection, but luckily, for all parties included, Mark didn't take offense easily. He shrugged it off like every other rejection from a woman.

So it just so happened that when Mark showed up, Anna made a supply run. His client had rescheduled, so he was free for an hour to pop in, and so Jack caught him up to speed with the smokescreen of being in a relationship with Anna. Telling him about the two of them _almost_ being serious, until Anna covertly rejected him by claiming to love her job too much to quit so that they could date. It was brutal, for Anna's standards.

But Jack was lucky to still call Anna his assistant. For all the hell he put her through by talking her into faking a relationship, he was surprised she would still work for him at all. But he guessed that she did it just to spite him, and just to prove a point. And Mark had been saying, "... You mean to tell me that she bailed on her boyfriend to hang out with you, then lied about it to save face, and you two _still_ aren't sleeping together?"

Jack shook his head. "See, for once you were wrong, my friend. There's nothing between us."

"Oh, I wouldn't say that," Mark contested, leaning back in his seat once more. "Sounds to me like this is Anna's desperate cry for help."

Jack furrowed his brow in confusion. "Desperate cry for... what?"

Mark rolled his eyes. "Anna _wants_ to be with you," he said. "But she doesn't want to admit that she made the mistake of hooking up with some loser, and doesn't want to admit that you're better for her. She can't stand to be wrong, but she _wants_ to be. So..." He shrugged, coming up with a counter measure. He snapped his fingers. "I've got it. You wanted a background check, right? _Do_ it. _Find_ solid evidence that this guy's a waste of her time."

"And you think... what? That if I prove to her this guy's a loser she'll come running to me?" Jack asked, rolling in his seat disbelievingly. Then he shuffled forward, leaning on his desk. "If I prove _anything_ to Anna by digging up dirt on Tim, it'll be that I'm a condescending asshole that thinks she can't handle her own problems. And she'll forever hold it against me that I tried to ruin her relationship."

"But if you find out this guy's a _fake_ , or some kind of _fugitive_ , she'll want nothing to do with him. And to who's waiting arms will she run to? _Yours_."

Jack rolled his eyes. "No, I'm not gonna do it," he detested. "I'm not gonna make a case against Tim."

"Not even if you had the best of intent?" Mark asked. "Not even if you were just doing it as a friend? To keep her from getting hurt? And what if she does, but _you_ could've prevented it? How bad is that going to make you feel, Jack? Pretty bad if you ask me."

Jack's jaw flexed at the thought. Mark knew where to hit him. It was true that he would feel terrible if something bad happened to Anna, but he could've stopped it. He would feel terrible if he let her get hurt all because he was trying to be the better guy. It was such a bad cliché, to air out Tim's dirty laundry for his own selfish gain, but to keep Anna from being swindled by this guy? Maybe it would be worth it to take the low road.

With a reproving glare at Mark, Jack swiped his cellphone from his desk, and scrolled through Anna's Facebook profile to her friend's list. He would not dare justify why Anna's profile was already pulled up. _Not_ that he'd been gazing longingly at her photos or anything. He stopped on the list when he found Tim Delaney, and tapped the photo, which was a team logo. Then he scrolled down the page for a moment.

No photos of Tim on his account. Nor were there any of his family. He'd told Anna his apartment caught fire, that's why he was remodeling. So all his pictures and keepsakes died in a tragic blaze. He ground his teeth, then pulled up his contacts and dialed a number. "Hey, Tom? Hey, it's Jack Bartlett." Mark sat forward in his seat, arching a brow. "So Tom, tell me... are you still working for the FBI?"

* * *

Some time later-precisely the time it took for Tom to check to see if Tim Delaney even existed-Jack was peddling his way through work when the office phone rang. Evelyn answered for him, listened for a moment, then pressed the phone to her shoulder and said over the comm, "Uh, Jackie, dear? Somebody named Tom Vance from the FBI is on the phone? Says he's found the guy."

Anna lofted a brow at her desk, as Jack paused what he'd been doing to pick up the blinking line. "Yeah, Tom? How's it going?" he asked.

A gruff voice on the other end of the line said, "You're Tim Delaney doesn't exist."

Jack glanced at Anna, and swallowed, before asking. "What do you mean?"

"I mean to say I took all the info you gave me, Jack, I put it into the system, cross-referenced our database, and this guy doesn't exist," Tom repeated, slowly, and in an irritated manner. "I can't run a background check on an imaginary person, Jack," he said. "So whoever this guy is, I guarantee you he's using a fake name on his account, because I've got several Tim Delaneys here but none of them are your guy."

Jack's mental engine reared to a complete halt.

Oh... _shit_.

"Well, thanks Tom, and I'm sorry I had to trouble you with this."

"No problem, Jack," was Tom's response, before he ended the call.

"Everything okay, Champ?" Anna asked him, and he blinked several times, trying to get the internal transmission to shift back into first. He looked down, and brushed an imaginary something off his tie.

"Uh, yeah, I just... something for a case."

Anna got up from her desk and walked over to his. "I don't remember any of your cases having anything to do with the FBI, Jack," she said, folding her arms. "What's going on?"

"Uh just... just a thought I had about one of our clients, and it turned out to be nothing anyway," he said. _Literally_ nothing. Tim Delaney was a phony. And she had no idea.

"Oh, okay, well," She stepped closer, "I was meaning to ask, do you think I could leave early today? It's Tim's birthday and I wanted to surprise him, so I thought I'd stop and get him a cake. I already sorted out your case files, and emailed your notes, plus Evelyn's got your drycleaning ticket, and everything's taken care of." She chewed her lip. "So is that okay? I mean, I know it's really last minute, but-"

"No, that's fine, whatever you want," he rushed to say, and she could tell something was wrong, giving him that look, but she didn't say anything.

"Okay, well, I've gotta get going then-"

"Wait," he said, scrambling to his feet, and Anna turned back to him.

His heart pounded in his chest. _Come on, Jack, just do it. Tell Anna about this guy. Dash all of her hopes and dreams by telling her Tim is a fake and has been lying to her._ Jack panicked for a moment, inwardly debating, all possible scenarios playing out in his head. There was the one where Anna hugged and thanked him for saving her from a disastrous relationship, confessed her love, quit her job, moved in, married Jack...

...And then there was the one where she didn't believe him, called him paranoid, and a jerk for meddling with her private life, slapped him, and stormed out. He'd chase her down, running out into the street and getting hit by a bus. She'd point, laugh and say, 'That's what you get for listening to Mark and being such a lying, conceited, self-serving asshole.' Which might be what he deserved for being such an idiot.

"Nevermind," he mumbled. "Have a great time with Tim tonight."

* * *

She stood in line for half an hour waiting for the cake, and because her car was still in the shop, she'd almost missed the bus. It was one of _those_ days. Added to the fact that Jack had been acting strange at the office, which threw her out of her groove, her stress level was already through the roof. Which was was she definitely needed this birthday surprise to pull off without a hitch.

She knew Tim's address because she'd overheard him taking a phone call in her bathroom, giving someone his home address, and she remembered it. So she proudly walked, head held high, two blocks from the bus stop to his apartment building, holding a cheery cake balanced in her arms. It was quite possible that a guilty conscience drove her to do this. She'd been neglecting a perfectly decent guy in favor of overindulging her needy boss.

She'd never been to this part of town before, and didn't know what to expect, but she certainly didn't picture such a run down complex. She was worried for a second that she had the wrong address. But she saw Tim's car parked nearby, and knew she was at the right place. She thought back to something Jack had said previously, but then dismissed the idea. There was no way Jack was right about him. No way.

She worked for one of the most successful lawyers in the city. She lived in a dump.

Tim was a consultant, but he lived here. So maybe they weren't that mismatched after all.

With a deep breath, she climbed the steps, nearly tripping when her phone buzzed in her pocket. She growled and balanced the cake on one arm to reach for it, checking the text. _Jack_. Saying, 'Can we meet up for coffee later? There's something I need to tell you.' Rolling her eyes and sighing, she pocketed the device without replying, and continued up the steps. Jack could wait for a change. It was what they both needed.

She thought it was a perfect candid moment for their relationship-their first birthday celebration-so she pulled out her cell to record Tim's reaction to her surprise. She ignored the text from Jack, saying, 'Anna please text me back, I really need to talk to you', and pulled open her camera, holding up the phone as she tried the doorbell. It didn't work, so she knocked on the door, and waited.

There was shuffling inside, and the door swung open.

To reveal a brunette twenty-something with bedhead, wearing a men's shirt, and nothing else. "Yeah, whaddya want?" she asked. Anna froze, speechless.

When she remembered there was a such thing as _words_ , she said, "I'm sorry, I... I think I have the wrong address. I'm looking for Tim? Tim Delaney?"

The brunette snorted. "Who the hell is Tim Delany?" she asked, as a man was coming up behind her.

"Babe who's at the door?" asked...

"Tim?!" Anna shrieked, dropping the birthday cake. The brunette gasped.

"Who the hell is she?! And why is she calling you Tim?!"

Tim gaped, mouth hanging open, before he rushed to say, "I don't know, I swear, I've never seen this woman in my life!" The brunette didn't look like she believed him. "Babe, I swear! I've never met this woman before!" Anna's mind was completely unable to process this, so she just stood there while the woman screamed at him before she remembered her phone was recording, and turned it off, slowly backing down the hall.

She turned and fled. Down the steps she went, almost tripping, so she kicked off her heels and carried them instead, flying out the door at a sprint. Where she was running to, she didn't know, but she stopped at the end of the block. Her car was still in the shop, and there were no more busses for the day on this route. She couldn't call Linda, as Linda worked a late shift, and she was stuck. Starting to tear up, she checked her phone and saw Jack's latest text.

'Are you ok? Please, Anna, let me know you're ok.'

She called him on the phone. "Anna, oh thank god, hey, I'm glad you finally called, I needed to-"

"Can you come get me?" she sobbed.

She squeezed her eyes shut as she heard a quiet, " _Shit_ ," on the other line. Then there was a loud noise that meant he dropped something, or slammed something, but she didn't know which. Then she heard, "Where are you?"

"I'm-I'm at Tim's. I just left his apartment-"

"Stay right there, I'm on my way."

* * *

His car reared to a screeching halt in front of Anna, and she practically dove for the passenger's seat. He didn't say a word, just pulled away, glancing at her every once in a while as he took them back to the other side of town. Something had happened, and he had a feeling that Anna had just learned the truth about Tim. She asked him to pull over at the overpass, and showed him the video.

He watched as Anna went to surprise Tim, but got a surprise herself, when some strange woman answered the door, and Tim pretended he didn't even know Anna. The video went on to show Tim and the other woman have it out with each other. He snorted a little when he saw Tim get bitchslapped before Anna stopped recording. He hated being right about this guy. He usually loved being right, but not this time.

"Go ahead, say it," she sniffed beside him as he handed her the phone. "Say 'I told you so'."

"I'm sorry," he said. She sobbed again.

"Oh god it all makes sense now," she said. "Why he only came to my place, why he 'lost his wallet' when we went out, probably because he didn't want me to see his driver's licence, or his credit card. And I never even questioned any of it. You were right, Jack, he was just using me, and I let him." She furiously scrubbed her face. "Oh god this is so embarrassing! I can't believe I let him use me like that. And what's worse is... I think I was the _side piece_."

"Anna, it wasn't your fault," he told her. But she didn't believe him. She still had that look of self loathing on her face. What he hated even more than being right, was seeing her upset like this. He was supposed to be the one falling apart, not her. He leaned and put his arm around her. "Hey, it's gonna be okay," he said, squeezing her shoulder. "You know, I have people I can call if you want this guy eating out of a dumpster for the rest of his life."

She leaned into the embrace, resting her head on his chest. "Thank you," she said. "For coming to get me. I'm sorry you had to leave the office for something as stupid as this."

"I'd do it again in a heartbeat," he told her, pulling her closer, both arms wrapped around her now and his chin resting in her hair. He could smell her perfume. Roses. She hated anything too musky, and anything citrus made her think of public bathrooms. Even worse was to smell like fabric softener, but she liked flowers. She always smelled great to Jack. "I was being serious, by the way. If you want this guy living in a cardboard box, you let me know."

She chuckled. "No, I-I think I'll be alright. Just take me home."

"You got it," he said, and she pulled away. She glanced up at him, wiping the last remnants of her waning emotions with her shirt cuff. He forced himself to turn the key in the ignition, start his car, and focus on the road. He took her back to her apartment and walked her to her door. They both slowed in step and shared a glance when they saw her door was cracked open, and she rushed ahead of him to get inside.

* * *

Anna marched through the living room and into the kitchen to see none other than Tim standing there, with her refrigerator door open, like he lived there. "Tim?!" She gaped at him, and he whipped around, shutting the door. For a moment he was a deer caught in the headlights before he walked toward her.

"Babe, I can explain everything," he said. She turned and walked back into the living room, shaking her head, hardly believing that of all things, he would show back up to her apartment, groveling. He followed her. "Please, it was just a misunderstanding. Look, she meant nothing to me, I swear. We're done. You're the only one I want to be with." She huffed and turned back to him.

"I'm guessing that was _her_ apartment, and she threw you out, so now you're running back to me." At that moment, Jack was crossing the threshold, having realized Tim was still in the picture, and he waltzed into the room, hands in his pockets.

"Who the hell is _this_?!" Tim shrieked. "Are you screwing this guy?"

"I don't think that's any of your business," said Jack, calmly. "Now, if you don't want the police involved and to get charged with breaking and entering, I suggest you leave. _Immediately_."

"B&E?" Tim stepped closer. "Bullshit. I've got a key." He pulled it out and held it up. Jack snatched the key to her flat out of Tim's hand.

"Not anymore you don't. Now get out." He pointed to the door. Tim puffed himself up, and Anna could see the look on Jack's face slowly morph from calm courtroom composure to something else. He glanced down. "Please don't make me do this," he said. Anna stood frozen as Tim stepped closer and shoved Jack's chest. Jack sighed. "Dammit," he cursed, then _punched_ him. Right in the stomach, and Tim doubled over.

Then fell backwards, right onto the coffee table, that snapped into pieces, when Jack floored him with a straight shot. Tim shrieked and blood poored down his face. "Oh my god, I think you broke my nose!" he cried. Anna, who had gaped in shock, suddenly burst out laughing at the sound of Tim whining like a two year old on the floor. Her eyes shifted from Tim to Jack, who was rolling his eyes.

 _Oh my god, I love this man_ , she thought. _Way to go, Champ!_

She'd never seen this side of Jack before. She supposed she was so used to seeing the guy that spilled ketchup on a new shirt, or chickened out when it came to women, that she never expected him to actually deck Tim. She didn't know he was that kind of guy. Tim scrambled to his feet and sidestepped around Jack to get away from him, tears streaming down his face. But he turned back in the doorway and said, "I'm gonna sue you for this!"

Jack grinned at Tim like the cat that ate the canary. "I'm a _lawyer_ , cupcake. You have fun with that." With one last pout, Tim, still clutching his nose, ran to the stairs and out of her building. "I'll see you in court!" Jack shouted after him. Then turned to Anna, spotting her mangled furniture. He handed her the key he'd taken, and she removed one of the hands cupping her mouth to take it. She could hardly breathe.

 _He punched a guy for me_. "When were you gonna tell me you're secretly a badass?" she asked, and he chuckled, shaking his head. "I mean, you really laid one on him." She stepped closer, checking to see if his hand was bruised. "I should get you some ice."

"It's fine," he told her.

"That's it, there's only one explanation for this. You're a spy."

"Nah, I've just seen the Rocky movies one too many times," he shrugged. She chuckled. His phone buzzed in his pocket just then, and he pulled it out. It was his mom calling. "Hey mom," he said when he answered. His eyes widened a touch. "Eight AM? Uh, yeah, I'll be there... Love you too. Bye." He hung up the phone, and swallowed. "Uh, Anna?" Her smile dimmed. _Oh no_ , she thought. _I know that look._

"Yeah, Champ?" she asked.

"Any chance you'll be my Adrien?"


	6. Long Island Getaway

"I can't believe you actually said _yes_ ," Linda huffed, Wednesday afternoon, in the discount dress shop next to Anna, as she sifted through hanger after plastic hanger of cocktail dresses.

"He _punched_ a guy for me, Lin, how could I possibly say no?" Anna asked, shoving yet another dress to the side.

Yes, Jack had _really_ outdone himself this time. Not only did he forget to mention that his _parents_ were flying in for the weekend, but it just so happened to slip his mind to tell them he "broke things off" with Anna. So as far as Mr. and Mrs. Bartlett knew, their fake relationship was still going strong. And what did Anna do about it? Told him, "Yes, I'll go to dinner and meet your parents." Like an idiot.

She was so caught up in Jack's heroics that any logical thinking had been overruled.

 _But oh my god he looked so hot punching Tim_ , she thought.

Suffice to say, Jack's parents were taking a red-eye, Jack would be waiting at the airport to meet them at 8 AM on Friday, and later, Mr. and Mrs. Bartlett would be meeting them both for dinner Friday night.

"And what are you supposed to do if he lays another one on ya?" Linda asked.

"We're limiting the PDA to hand holding," Anna told her, and slid another hanger to the side. Linda snorted. "What was I _supposed_ to do, Lin? He made the _face_. I can't say no when he makes that face, and at least I don't have to worry about how 'Tim' feels about it. I'd just assume that prick never existed. Which apparently won't be that difficult... It's just dinner. It's not like we're getting _married_."

Linda chuckled. "Heh, yeah, well, at _this_ rate... So where are you meeting his parents?"

Anna sighed.

The most expensive restaurant in the city. But at least she wasn't the only one sweating over that detail. So was Jack. But his parents were loaded, Mr. Bartlett was very devoted to his wife, and wanted only the best for Mrs. Bartlett. The guy was so much of an overachiever when it came to women that he gave his son some competition in the field. He _really_ loved his wife, perhaps just a little too much.

Which was why Anna was taking her lunch hour to shop for a dress that _looked_ expensive, but wasn't _actually_ expensive. And so far all she'd managed to find for a good price were sleazy little cocktail dresses, or last season pant suits. "Oh, honey, if I still had your figure," said Linda as she snatched a hanger off the rack and held the dress up to Anna's frame. Something Anna would _never_ wear. "Why not just go to Bloomingdales?"

"Because I'm still bailing myself out of debt," Anna groused. "And one dinner with the Bartletts is not enough to convince me to sink further into it."

"Why not just use Jack's credit card?" Linda suggested, and Anna shook her head.

"Absolutely not."

"And _why_ not? They're _his_ parents, this was _his_ idea, and you're posing as his _girlfriend_. By all rights, that gives you _every_ excuse to spend his money." Anna clucked and turned back to her shopping, shaking her head. "He's taking the already inappropriate work relationship to a whole other level here, sweetie. All because he's so bad with break-ups that he can't even call off a _fake_. Don't you think he _deserves_ to be given a lesson?"

Anna shrugged. "Maybe? I don't know. But I'm certainly not going to get even with him by committing credit card fraud."

"Hmph, _well_ ," Linda held up the cocktail dress. "There might be _another_ way you can do it."

* * *

Jack checked the time, then scratched his head.

She was late. Anna Baker was  _never_  late.

He'd pulled up outside the restaurant, tossed the valet the keys, and then stood there, for almost _twenty minutes_ , while his parents waited inside. He was starting to think she stood him up, but breathed a sigh of relief when he saw a cab pull up next to the entrance, and watched as a woman with wavy chestnut locks stepped out. But then he stopped breathing when he got a look at what she wore.

Anna, _his_ Anna, stuck one spiked heel out of the car, then the other, and his eyes traveled from her shoes, all the way up two long, shapely legs, to a white lace dress that _barely_ covered her ass, hugged her curves, and showed off her two most _voluptuous_ assets. He swallowed the lump in his throat when she approached the driver's side window, bent forward, and paid the cab fare.

Anna Baker looked _hot_. And Jack Bartlett was a dead man.

She stood up as the cab pulled away, and flipped her hair over one shoulder, then waltzed up to him, showing not only how much make-up she was wearing, but giving him a _spectacular_ view of body parts he absolutely should _not_ be ogling. He was so used to seeing Anna wear such modest skirts and blouses, or dress down in a t-shirt and jeans. He'd never seen her this put together, but at least now he knew why she'd been late.

She walked up to him with a smug grin that told him she'd done it on _purpose_ , saying, "Hey, Champ," and immediately reaching for his tie that suddenly felt like it was strangling him, coming to stand _dangerously_ close, pushing her chest out, and he made the mistake of glancing down. _I'm going to die now_ , he told himself, as he caught sight of two stunning twins nestled in her bra, and forced himself to look away.

"There we are," she cooed when his tie was secure.

He cleared his throat, and said, "Shall we?" Then he held out his arm.

* * *

Anna smiled in spite of herself, and her untoward behavior. It seemed Linda's plan was already working, as Jack looked pretty put off by how skimpy her outfit was. How much she'd dolled herself up, and how late she was, arriving at the restaurant. He looked like any minute now he'd sweat right out of his suit. He hated when women did things like that. Dressed like hookers and acted like tramps, which was _exactly_ what Anna intended to do.

To teach Jack a lesson, Anna would be the worst date possible this evening.

They walked into the restaurant, Jack looking like a million dollars and Anna looking like a hot mess, to spot an older couple across the waiting area, rising to stand. And there they were. Mr. and Mrs. Bartlett, she presumed, when the woman came trotting over, squealing at the sight of her baby boy, stretching out her arms for a tight squeeze of a hug. "Oh it's so good to see you, sweetheart!" she said, embracing him.

"Hey, mom," Jack choked out when her arms snaked around his neck like a python and strangled him mercilessly. Anna snickered a little. Debra was exactly what Anna had pictured in her mind. Overbearing, but so full of love. She looked absolutely stunning for sixty, and Anna could imagine why Jack Sr. still had undying adoration for his wife. She sported a savvy pant suit in plum with matching pumps, and totally _rocked_ it.

"Oh this must be Anna!" she said excitedly, and Anna was tackled next with a suffocating hug that caught her off guard. She let out a laugh. "Oh it's so nice to finally meet you," Debra wailed, "Let me get a look at you." She backed up a little, clutching her shoulders and looking her over. "My goodness, Jackie, you said she was pretty, but you undersold! Honey you're a knock-out!"

"Thank you," Anna managed with a smile, before her eyes shifted to Jack Sr.

She could definitely see where Jack got his looks from. If she were even _remotely_ interested in exceedingly older men, she would be all over this guy. Tall, dark graying hair, that derisive courtroom stare that Jack apparently inherited from _him_ , and though he had just a touch of a stomach sticking out over his belt, he was still in pretty good shape for his age. He mirrored Jack just then, as both stood with their hands in their pockets, staring.

"Dad."

"Son."

And that was the _extent_ of conversation between them.

Things got really awkward for about a half a minute, until Debra swooped in with, "Well, how about we get seated, hmm?" Then she flagged down the hostess. Reservations had already been made, so there was no further wait to be seated, and so they were led to a table for four, and Debra insisted she slide into the seat next to hers, across from Jack Sr., and beside Jack. Their server asked about drinks, and Anna smirked.

"Hmm, lemme think," she said, furrowing her brow and pretending to think really hard. "Oh! I'll have a Long Island," she said to the waitress, who nodded.

"Uh, _darling_ , you know there's _alcohol_ in a Long Island iced tea, right?" Jack asked sweetly, between his teeth. " _A lot_."

"Well, that's the _point_ , silly," she laughed, patting his elbow.

"But... _sweetheart_ , you _don't normally drink,_ " he reminded, but Debra cut in.

"Oh, sweetie, let her have some fun," she said. "Matter of fact, I think I'll have the same. No, you know what? Make mine a double."

Anna gasped. "Great idea. I'll have what she's having."

"Two double Long Islands on the double!" Debra proclaimed with a laugh.

It was Mr. Bartlett's turn to flush completely of color, but he said not a word, merely smiled tightly, and closed his drink menu. "Water for me," he said.

"I'll have the same," Jack added. The waitress lofted a brow.

* * *

Jack constantly fought the urge to loosen his strangling tie. He knew _exactly_ what she was up to. She was doing everything he knit-picked about on all his dates, everything he despised about women, and she was doing it on purpose. Wearing such a revealing outfit to meet his parents, overindulging when she normally wouldn't, and when he wasn't sweating over Anna's screwball behavior, he was sweating over the prices.

Oh yes, this was payback. In full.

When the drinks came, and the server asked what they would like to order, why, Anna ordered the most expensive items on the menu. She upped his stress factor by two hundred percent that night, all with a smile on her face. "...And _then_ , he told her she looked like a paint-by-number!" she snickered, making his mom bark with laughter and slap the table. "She threw her drink at him and stuck him with the bill!"

Oh yeah, to make matters worse, she spilled _everything_. Thank god she didn't mention she was his assistant, or that they were fake-dating, but Anna the light-weight Champion of Long Island, loaded every bit of ammo she had in her arsenal, and aimed it at his mother. Told her all about Jenna, Krystal With A K, the Pre owned Mercedes, as well as many other bad dates Jack had been on before they "found one another".

Beside him, his dad kept his composure, smiling politely and nodding as if interested in their gossip, occasionally arching a brow, but said absolutely nothing. Jack sweat over that too, because he _knew_ that he would hear it eventually. All about how much of an embarrassment Anna was, and how disgraceful it was to bring a woman like her to an establishment such as this one. But, luckily, she and his mom seemed to be getting along fine.

At least there was that.

But then again, his mom was _also_ vacationing in Long Island, and deep sea diving into her third glass. Jack smeared a hand across his face when she brought out _baby pictures_ saved on her iPhone.

"Oh he's so cute!" Anna squealed. "He looks like a little Cabbage Patch doll!" she cooed, reaching across the table to pinch his cheek. He faked enthusiasm and smiled, hearing his dad snort, but then cover it up with a cough.

"So, how's work treating you?" Dad finally asked, striking up conversation.

"Uh," Jack scratched his head. "Good. I-It's good."

"Good," he repeated with a nod.

The hens continued to cluck on the other side of the table. "Oh and this one's Lizzy at her recital," Mom had been saying. Anna put a hand to her chest and mouthed an 'Aw'. "They did the Nutcracker. She was the star of the show that year. But you know, she would take any part they gave her, she never cared. She just loved ballet so much! One year she was a tree, and she still got a standing ovation. I was so proud!"

"Oh and to think she's getting _married_ this year!" Anna gasped.

"Oh that reminds me, pumpkin," Mom leaned closer to Dad. "Liz and Steve bumped their wedding to the _following_ week. So we're going to have to call the caterer and the florist. Don't let me forget." She turned back to Anna. "So you're coming to Lizzie's wedding right? Oh Jackie, you need to bring her, Liz is going to _love_ her." Anna turned to Jack and grinned. "Oh, and I think she has room for one more bridesmaid!"

"Yeah, put her on the end," Dad said. "That way if things don't work out, you can crop her out of the photo." Neither Anna nor his mother caught what he was saying, too engrossed in conversation, but Jack caught it. He flexed his jaw. "So, how did you get lucky enough to find _this_ one, Sport?" he derided sarcastically, with a smile. Jack heaved a sigh, and smiled right back, leaning forward in his seat.

"It just _hit me_ , ya know?" he said, repeating the very same words Jack Sr. used when asked how he fell in love with Debra Worthing. "Like a _bus_ ," he added, then flopped back in his seat. His father narrowed his eyes, and so did Jack.

The check couldn't come soon enough.

And when it _finally_ did, Jack reached, but his dad managed to snag it first, slipping his credit card into the billfold without even _glancing_ at the total. He smiled up at the waitress, then eyed his son condescendingly. "You can get the next one, Sport," he said, with a wink. Jack clicked his teeth. Well at least that was _one_ crisis averted, and he didn't have to sweat over the check anymore, but Jack Sr. did it on purpose, just to prove a point.

That money would never have been an object, and that Jack wouldn't have to bat an eyelash about these types of things had he taken his offer to join the family firm. That he would've been set for life. Had he simply taken everything that was handed to him, instead of having a _realistic_ outlook on life that working for minimum wage had given him. So, like he always did, Jack simply nodded and thanked him.

"Oh, is it time to go?" Debra whined. "Oh that's too bad. We were having so much fun."

Anna nodded in agreement, and all four stood up from the table, Mom and Anna linked arm-in-arm. "Matter of fact," Dad said as they left the table, "How about you buy the two of us lunch tomorrow? There's something I've been meaning to talk to you about."

"Yeah, sure, sounds great," Jack nodded, absently rubbing the back of his neck.

Outside the restaurant, Anna was given another suffocating hug by his mother, who then leaned on her husband for support while they waited for their rental car. At that moment Jack realized she had been the only thing holding Anna up, who then slid her arm around Jack's midriff and leaned heavily on him. She was drunk, apparently. No surprise there. One glass of wine, and Anna was a freshman at a college mixer all over again.

He put his arm around her shoulder and both waved as his parents took off down the road, then his Audi pulled up in the spot where the Lexis had been. _God, what a night_ , he thought, then helped a giggling Anna into the passenger's seat. The whole way back to her apartment she went on and on about how _wonderful_ his mother was, and how _attractive_ his _father_ was, saying now she understood who the good looks were credited to.

But then, as he pulled up into a parking spot outside her building, she burst into tears, and the night took a turn for the worst. "I can't believe he would do this to me!" she sobbed. "This was supposed to be _Tim's parents_!" Jack sighed. Then he took off his seatbelt and leaned on the armrest, while Anna got it out of her system. "And instead I'm stuck pretending to be my _boss's girlfriend_ while he's out screwing every woman in town." She hiccupped.

"Oh boy," he mumbled.

She cried for another ten minutes before finally wiping her eyes, smearing her already ruined make-up, and Jack got out of the car to help her out of her seat. She leaned on the door after it closed and pouted. "Are you mad at me?" she asked. Again, he could do no more than sigh, neglecting to comment. "You _are_ mad at me," Hiccup, "Aren't you? You're making the 'Anna, you really fucked up,' face and you _hate_ me now."

"No, I don't _hate_ you," he swore, shaking his head, slipping his arm around her shoulder. "Let's get you upstairs."

His only saving grace was knowing how his egotistical, overbearing, controlling and insufferable father was going through this very same thing with Mom on the other side of town, and he quirked a brow at the thought. He held Anna upright and carried her neck breaking shoes while she shuffled up the steps beside him. "I don't know why he can't be more like _you_ ," she huffed. "You're _perfect_ , and you eat M&Ms with me."

"Do what now?" he asked.

" _You_ , I wanted Tim to be _you_ ," she whined. "You're like my _best friend_. But don't tell Linda I said that, 'cause she'll get jealous." Another flight of stairs and they reached her door. She slumped against the wall while he dug through her purse for her key, lost in the myriad of receipts and extra napkins from too much fast food and too many take-outs. "And you do all these nice things for me," she told the floor, while he searched.

He finally found the key, and unlocked the door. Meanwhile, Anna was lolling her head and wallowing in self pity still, and he sighed at the sight of her. He cupped her shoulders and said, "Hey, look at me," Making her tear streaked face tilt upward, and big red rimmed brown eyes peer up at him. "It's gonna be alright. You just need to sleep it off. You'll feel better in the morning." He rubbed her shoulders, thumbs caressing her skin.

He really wasn't expecting her to _leap_ at him, loop her arms around his neck and _kiss_ him. He was startled by it, heart racing in his chest, knees buckling at the sound she made, and next thing he knew, he was shoved against the wall, with the woman to whom his heart belonged pressing against him, kissing him passionately, and he shivered when her nails scraped his scalp. _Oh dear god, Anna is making out with me!_

For a solid ten seconds he forgot where he was, and what he was doing, as his hands roamed over her back and his tongue searched for hers. It didn't take that long to get hard, not after being tortured all night by that sexy skin-tight dress, or the way she smirked and bit her lip whenever she looked his direction that night. His hands found her ass, that felt _great_ under the smooth fabric, and she moaned in his mouth when he squeezed.

" _Shit_ ," he breathed when she tore her mouth from his, tugged his head back and kissed along his neck, her other hand finding his tie and loosening the torture device. Then her hands slipped down to his collar, and started to unbutton his shirt. It was then that it clicked in his mind, smelling alcohol, remembering how much she had to drink, and how she would never act like this, were she sober. "Anna, wait," he panted, pushing her at arms length.

" _Please_ , Jack," she begged. "I can't take it anymore. I _need_ you."

 _Fuck_.

He'd fantasized about hearing her say those _exact words_ , time and time again. "Dammit," he quietly cursed. He couldn't do it. He couldn't take advantage of her like this. He _had_ to do the right thing. She started to unbuckle his belt, but he caught her hands in his and held them at bay. "Anna, we can't do this. You've had a lot to drink tonight. You're just-just upset about that douchebag still, that's all. You need to sleep it off."

She pouted for a minute, then flopped her head against his chest, saying, " _Dang it!_ Why do always have to be so nice?... Even when I don't want you to be?"

 _Maybe because I don't want to be that kind of guy and I love you_, he'd thought of saying, but didn't. She'd forget all about this come Monday, anyway. And even if she _did_ remember, she damned sure wouldn't bring it up. Provided she even showed up at the office, or ever spoke to him again. He pushed her to stand up straight and nudged her toward her apartment door, handing her the key, then her purse, and finally her shoes.

She made a wounded puppy face at him, before closing the door, saying, "G'night, Champ."

"Goodnight," he told her, and sighed once she was inside.

He had to have had the _worst_ kind of luck.

He had the woman of his dreams throwing herself at him, but couldn't take the shot.

"What even _is_ my life," he groused.

Then he slumped against the wall, twirling his keys around on his index finger for a moment, before descending the stairs, shaking his head...

...Back at his apartment, in the garage, he slammed his head into the steering wheel, setting off the horn. Dogs barked down the street, but he couldn't bring himself to care how much of a disturbance he might've been causing. When he was done having his pity party, he peeled out of his car, slamming the door, running a hand through his hair. He kicked the fender, then stomped upstairs.

He could hear Mark in his head, saying, "What the hell is _wrong_ with you, man?! She _finally_ hands you the keys to the kingdom and you _walk away_?! You could be in her apartment right now, puttin' the moves on your dream girl, but where are you? Home alone with a bottle of whiskey and a tub of ice cream. Like a _dumbass_... You deserve every ounce of your misery, my friend."

He slammed his head in the freezer door a few times before flopping down on his couch, and staring up at the ceiling.

On the flipside, he could imagine what Anna would be telling him. "...Thanks, Champ. You're my hero. I really needed you to do the right thing tonight, and I'm so glad you did. I know I was acting like I wanted you so badly, but the truth is I _don't_ want to be with you, I will _never_ want to be with you, and had we slept together, it would've been the _worst_ decision I ever made. You didn't take advantage of me, even though it was tempting. Great job."

He scoffed aloud at Anna's condescending tone in his head, before slipping off the couch to walk across the apartment and into his bed, stuck laying awake that night without so much as the ability to text Anna and see if she wanted coffee.

He _never_ should've asked Anna to pose as his girlfriend.

After what _almost_ happened earlier, he had no choice but to come clean to his parents now.


End file.
